Category: 6959-48-4

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Application In Synthesis of 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.3 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-pent-4-enoate (S)-Enantiomer, ((S)-15): Yield: 750 mg (55%), white solid. Mp 176-177 C. 1H NMR (300 MHz, CDCl3): delta 1.31 (s, 9H), 2.27 (ddd, 2JH,H = 14.7 Hz, 3JH,H = 8.0 Hz, 3JH,H = 6.9 Hz, 1H), 2.49 (dt, 3JH,H = 13.8 Hz, 3JH,H = 6.9 Hz, 1H), 3.86 (s, 3H), 4.49 (d, 2JH,H = 16.1 Hz, 1H), 4.51 (t, 3JH,H = 7.5 Hz, 1H), 4.69 (d, 2JH,H = 16.6 Hz, 1H), 4.89 (dd, 3JH,H = 17.1 Hz, 2JH,H = 1.5 Hz, 1H), 4.99 (dd, 3JH,H = 10.2 Hz, 2JH,H = 1.5 Hz, 1H), 5.60 (ddt, 3JH,H = 17.0 Hz, 3JH,H = 10.3 Hz, 3JH,H = 6.7 Hz, 1H), 6.94 (dm, 3JH,H = 9.0 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.9 Hz, 1H), 7.73 (dm, 3JH,H = 9.0 Hz, 2H), 7.86 (d, 3JH,H = 7.9 Hz, 1H), 8.50 (d, 3JH,H = 4.0 Hz, 1H), 8.54 (d, 4JH,H = 1.7 Hz, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.8 (q), 35.5 (t), 46.6 (t), 55.6 (q), 60.2 (d), 82.3 (s), 114.1 (d), 118.4 (t), 123.3 (d), 129.6 (d), 131.5 (s), 133.0 (d), 133.7 (s), 136.6 (d), 148.5 (d), 149.0 (d), 163.0 (s), 169.3 (s) ppm. HRMS (ESI+): C22H28N2O5S+H+, calcd 433.1797, found: 433.1812; C22H28N2O5S + Na+, calcd 455.1617, found: 455.1630, (C22H28N2O5S)2+H+, calcd 865.3516, found: 865.3532; (C22H28N2O5S)2 + Na+, calcd 887.3336, found: 887.3345. Optical rotation (c 1.001, CHCl3): [alpha]58920 = -26.4, [alpha]57820 = -27.3, [alpha]54620 = -31.2, [alpha]43620 = -56.6, [alpha]36520 = -97.7.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 3-(Chloromethyl)pyridine hydrochloride

General procedure: DMF (5-10 mL/mmol). K2CO3 (10 equiv) was added and the suspensionstirred for 15 min. Then, 3-(chloromethyl) pyridiniumchloride (1.1 equiv) was added and the reaction mixture was stirredfor 48 h at room temperature. The suspension was diluted withH2O and extracted with EtOAc. The combined organic phases werewashed with H2O and brine, dried over magnesium sulfate and thesolvent was removed in vacuo. The crude products were purifiedby column chromatography [Cyclohexane/EtOAc, 3:1 4.2.2.2 tert-Butyl N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-amino-4-fluorobutanoate (S)-Enantiomer ((S)-14): Yield: 1512 mg (85%), greenish, viscous oil. 1H NMR (300 MHz, CDCl3): delta 1.35 (s, 9H), 1.86 (m, 1H), 2.22 (ddt, 2JH,H = 13.6 Hz, 3JH,H = 9.7 Hz, 3JH,H = 6.0 Hz, 1H), 3.86 (s, 3H), 4.19-4.45 (m, 2H), 4.36 (d, 2JH,H = 16.1 Hz, 1H), 4.49 (dd, 3JH,H = 7.7 Hz, 3JH,H = 6.6 Hz, 1H), 4.69 (d, 2JH,H = 16.2 Hz, 1H), 6.96 (dm, 3JH,H = 8.9 Hz, 2H), 7.25 (dd, 3JH,H = 7.9 Hz, 3JH,H = 4.8 Hz, 1H), 7.77 (dm, 3JH,H = 8.9 Hz, 2H), 7.82 (dm, 3JH,H = 8.4 Hz, 1H), 8.51 (s, 1H), 8.53 (s, 1H) ppm. 13C NMR (75 MHz, CDCl3): delta 27.7 (q), 31.8 (dt, 2JC,F = 20.5 Hz), 47.3 (t), 55.6 (q), 57.0 (dd, 3JC,F = 4.3 Hz), 80.1 (dt, 1JC,F = 166.3 Hz), 82.5 (s), 114.1 (d), 123.4 (d), 129.6 (d), 131.3 (s), 132.9 (s), 136.3 (d), 149.1 (d), 149.4 (d), 163.0 (s), 169.0 (s) ppm. 19F NMR (282 MHz, CDCl3): delta -221.4 (ddt, 2JH,F = 46.9 Hz, 3JH,F = 28.3 Hz, 3JH,F = 22.8 Hz) ppm. HRMS (ESI+): C21H27N2O5S+H+, calcd 439.1703, found: 439.1701; C21H27N2O5S + Na+, calcd 461.1522, found: 461.1526; (C21H27N2O5S)2+H+, calcd 877.3328, found: 877.3320; (C21H27N2O5S)2 + Na+, calcd 899.3147, found: 899.3146. MS (ESI+, daughter ion experiment): m/z (%) 439 (15) [M++H+], 383 (100) [439-C4H8], 171 (5) [C7H7O3S+], 167 (10) [383-C7H7O3S-CO2H], 92 (3) [C6H6N+]. Optical rotation (c 1.001, CHCl3): [alpha]58920 = +34.1, [alpha]57820 = +35.5, [alpha]54620 = +41.1, [alpha]43620 = +74.5, [alpha]36520 = n.d.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Behrends, Malte; Wagner, Stefan; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Kumbhar, Sadhana; Waller, Mark; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3809 – 3818;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6959-48-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Reference Example 22 N-(4-Bromophenyl)-N-((pyridin-3-yl)methyl)pyrimidin-2-amine [Show Image] Under an argon atmosphere, N-(4-bromophenyl)pyrimidin-2-amine (200 mg) was added to a suspension of sodium hydride (48 mg) in anhydrous DMF (8 ml), and the resulting mixture was stirred at room temperature for 30 minutes. The reaction solution was cooled to 0C, and 3-chloromethylpyridine hydrochloride (600 mg) and triethylamine (1.00 ml) were added thereto, followed by stirring the resulting mixture at room temperature for 2 hours. Saturated brine was added to the reaction solution and the resulting mixture was extracted 3 times with ethyl acetate. Organic layers were washed 3 times with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: ethyl acetate/hexane = 3/1) to obtain N-(4-bromophenyl)-N-((pyridin-3-yl)methyl)pyrimidin-2-amine (232 mg). NMR(H1, CDCl3):delta 5.23(2H, s), 6.65(1H, t, J=4.6Hz), 7.08-7.12(2H, m), 7.20(1H, dd, J=7.8, 4.9Hz), 7.46-7.50(2H, m), 7.59-7.61(1H, m), 8.35(2H, d, J=4.6Hz), 8.49(1H, dd, J=4.9, 1.5Hz), 8.54(1H, d, J=2.2Hz)

According to the analysis of related databases, 6959-48-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Toray Industries, Inc.; EP2033637; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6959-48-4 ,Some common heterocyclic compound, 6959-48-4, molecular formula is C6H7Cl2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

A suspension of calixarene 1 (0.17 g, 0.40 mmol), K2CO3(1.77 g, 12.8 mmol) and 3-(chloromethyl)pyridine hydrochloride (0.52 g, 3.2 mmol) in anhydrous CH3CN (10 ml) was stirred under nitrogen at 508C for 20 h. The reaction mixture was quenched with water and the residue was collected by filtration, dissolved in CH2Cl2 and washed withaNa2CO3 solution. The organic solvent was removed under reduced pressure and the residue was purified by column chromatography (SiO2;CH2Cl2 to CH2Cl2/ CH3OH, 95:5). The pure final product was obtained with a 51% yield (0.13 g).1H NMR (CDCl3,278C, 500 MHz): d 8.77 (s, 2H, H8),8.63 (d, J 5.0 Hz, 2H, H11), 8.06 (d, J 7.7Hz,2H, H9),7.57 (s, 2H, H6), 7.25 (dd, J1 7.7Hz, J2 5.0Hz, 2H, H10), 7.09 (d, J 7.6Hz, 4H, H4), 6.83 (d, J 7.6 Hz, 4H, H2), 6.71 (t, J 7.6 Hz, 4H, H1, H3),5.08 (s, 4H, H7), 4.26 (d, J 13.0 Hz, 4H, H5ax), 3.38 (d, J 13.0 Hz, 4H, H5eq). 13CNMR (CDCl3,278C, 125MHz): d 153.10, 151.51, 149.69, 148.78, 135.44,133.00, 132.25, 129.21, 128.58, 127.79, 125.77, 123.93, 119.25, 75.71, 31.41. ESI-MS: m/z 607 [M H], 629 [M Na]. UV- vis absorption (CH3CN, l268 nm): 1 7275M21 cm 21

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6959-48-4, 3-(Chloromethyl)pyridine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bonaccorso, Carmela; Nicoletta, Francesca; Zito, Valeria; Arena, Giuseppe; Sciotto, Domenico; Sgarlata, Carmelo; Supramolecular Chemistry; vol. 25; 9-11; (2013); p. 615 – 625;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, the common compound, a new synthetic route is introduced below. Safety of 3-(Chloromethyl)pyridine hydrochloride

To a stirring solution of 4-(1-tert-Butoxycarbonyl-2-methyl-propylsulfamoyl)-benzoic acid methyl ester (Compound 1*-884 mg, 2.38 mmol) in dimethylformamide (30 ml) at ambient temperature was added cesium carbonate (10.86 g, 33.34 mmol). Then 3-picolyl chloride hydrochloride (546 mg, 3.33 mmol) was added to the suspension and the reaction mixture was stirred at room temperature for 24 hours by which time TLC (EtOAc/Hexane 1:1) monitoring showed the reaction to be completed. The mixture was evaporated to dryness and the residue was stirred in ethyl acetate (50 ml). The ethyl acetate phase was extracted with water (1×50 ml), dried (MgSO4), filtered and evaporated to afford the crude product as a brown oil. This oil was purified by flash chromatography to furnish the pure product as colourless oil. Yield 800 mg (79.21%).

The synthetic route of 6959-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Storey, Anthony; Davis, Julie; Ricketts, Sally-Ann; Medizabal, Marivi; Cuthbertson, Alan; Arukwe, Joseph; Heywood, Kirsty; Wilson, Ian; Wynn, Duncan; Schafers, Michael; Levkau, Bodu; Wagner, Stefan; Breyholz, Hans-Jorg; Kopka, Klaus; US2007/71670; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6959-48-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of4(1.00 eq.) in DMF was added K2CO3(1.20-2.00 eq.). The reaction was stirred at room temperature for 1 h, followed by the addition of the alkyl halide (1.00-1.10 eq.). The reaction was stirred at room temperature for 0.5-24 h, concentrated under reduced pressure and purified by flash column chromatography (silica gel, solvent system I: petroleum ether ramping to 100% EtOAc, or solvent system II: DCM ramping to DCM/MeOH = 97:3) to give the desired product.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 6959-48-4, 3-(Chloromethyl)pyridine hydrochloride.

Reference:
Article; Diab, Sarah; Abdelaziz, Ahmad M.; Li, Peng; Teo, Theodosia; Basnet, Sunita K.C.; Noll, Ben; Rahaman, Muhammed H.; Lu, Jingfeng; Hou, Jinqiang; Yu, Mingfeng; Le, Bich T.; Albrecht, Hugo; Milne, Robert W.; Wang, Shudong; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 762 – 772;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6959-48-4, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 6959-48-4 as follows.

Step C: Preparation of Diethyl 2-(1-(pyridin-3-yl)propan-2-yl)malonate. To a suspension of diethyl methyl malonate (1.80 g, 10.2 mmol) in DMF (25 ml) at 0 C. was added sodium hydride (1.25 g, 31.0 mmol, 60%), followed by 3-(chloromethyl)pyridine hydrochloride (2.00 g, 12.2 mmol) and stirred for 8 h at room temperature. The reaction mixture was quenched with acetic acid and extracted with ethyl acetate. The combined ethyl acetate layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 2.50 g (91.2%) of diethyl 2-(1-(pyridin-3-yl)propan-2-yl)malonate as pale brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6959-48-4, its application will become more common.

Reference:
Patent; Zeitlmann, Lutz; Niestroj, Andre; Heiser, Ulrich; US2011/224225; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Recommanded Product: 3-(Chloromethyl)pyridine hydrochloride

General procedure C: A suspension of 2-morpholino-naphth[2,1-e]-1,3-oxazine 10b, 13b, and 13c (1 mmol), cesium carbonate (8.5 mmol) and 2-(bromomethyl)-pyridine hydrobromide, 3-(chloromethyl)-pyridine hydrochloride (2 mmol) in acetonitrile, according to the previously reported procedure.10 The solid was collected and recrystallised from a suitable solvent.

With the rapid development of chemical substances, we look forward to future research findings about 6959-48-4.

Reference:
Article; Ihmaid, Saleh; Al-Rawi, Jasim; Bradley, Christopher; Angove, Michael J.; Robertson, Murray N.; Clark, Rachel L.; Bioorganic and Medicinal Chemistry; vol. 19; 13; (2011); p. 3983 – 3994;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.6959-48-4, name is 3-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, molecular weight is 164.03, as common compound, the synthetic route is as follows.Application In Synthesis of 3-(Chloromethyl)pyridine hydrochloride

A mixture of ethyl 3-[3-ethoxy-1-(4-hydroxy-3-methoxybenzyl)-1H-pyrazol-4-yl]propionate (505 mg), 3-picolyl chloride hydrochloride (476 mg), potassium carbonate (601 mg) and N,N-dimethylformamide (10 ml) was stirred overnight at room temperature. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and then with saturated brine, dried (MgSO4) and concentrated. The residue was applied to silica gel column chromatography and compound G (531 mg, yield 83%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. NMR(CDCl3)delta:1.21 (3H, t, J=7.0 Hz), 1.37 (3H, t, J=7.0 Hz), 2.47-2.55 (2H, m), 2.61-2.69 (2H, m), 3.84 (3H, s), 4.09 (2H, q, J=7.0 Hz), 4.22 (2H, q, J=7.0 Hz), 4.99 (2H, s), 5.13 (2H, s), 6.68 (1H, dd, J=8.0, 2.2 Hz), 6.77 (1H, d, J=2.2 Hz), 6.84 (1H, d, J=8.0 Hz), 6.95 (1H, s), 7.31 (1H, dd, J=8.0, 4.8 Hz), 7.79 (1H, dt, J=8.0, 1.8 Hz), 8.57 (1H, d, J=4.8 Hz), 8.67 (1H, s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6959-48-4, 3-(Chloromethyl)pyridine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1445254; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem