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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. 93683-65-9, name is 6-Chloro-3-nitropicolinonitrile, molecular formula is C6H2ClN3O2, 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. category: pyridine-derivatives

Method A: To a solution of delta-chloro^-cyano-S-nitro-pyridine (3.03 g, 16.5 mmol) in ethanol (166 ml) and H2O (16 ml) was added iron (165 mmoi, 9.2 g) and calcium chloride (2.75 g, 24.8 mmol). The reaction mixture was refluxed for 4 hours and then cooled down to room temperature. The precipitate was filtered off over Celite and the filtrate was evaporated to dryness. The residue was redissolved in ethyl acetate and extracted with brine. The aqueous layer was extracted back with ethyl acetate. The combined organic layers were evaporated in vacuo. The residue was adsorbed on silica and purified by silica gel column chromatography, the mobile phase being a ethyl acetate/hexane mixture in a ratio of 3:7, resulting in the pure title compound (1.89 g, yield 67 %) which was characterised by its mass spectrum as follows: MS (m/z): 172, 174 ([M+H]+, 100).Method B: To a suspension of 6-chloro-3-nitro-pyridine-2-carbonitrile (9.2 g, 50 mmol) in water (100 ml), was added 20 ml of a 25 % ammonia aqueous solution. The mixture was stirred at room temperature for 20 minutes. Then, Na2S2O4 (50 g, 86 %, 150 mmol) was added portion wise, and the mixture was stirred at room temperature for another 2 hours. The precipitate formed was collected by filtration, washed two times with cold water (10 ml) and then dried over P2O5, resulting in the title compound (7.0 g, yield 81 %) as a yellowish solid which was characterized by its mass spectrum as follows: MS (m/z): 172.1 ([M+H]+, 100).; Example 222 – synthesis of S-amino-e-chloro-pyridine^-carboxamideEither of the two following methods may be used:Method A: to a suspension of theta-chloro-S-nitro-pyridine^-carbonitrile (4 g, 22 mmol) in water (40 ml) was added a 33 % aqueous solution of ammonia in water (8.8 ml). This suspension was stirred at room temperature for 30 minutes. Then, sodium dithionite (21.8 g, 124 mmol) was added portion wise. The resulting mixture was stirred for another 2 hours at room temperature. The precipitate was filtered off and washed with a small amount of water, yielding the title compound (2.7 g, yield: 72 %). MS (m/z): 172, 174 ([M+H]+, 100).Method B: to a suspension of e-chloro-S-nitro-pyridine^-carbonitrile (11.01 g, 60 mmol) in methanol (120 ml), was added Raney-Nickel (3 g, washed with methanol EPO to remove water) and the mixture was shaken under a H2-atmosphere at room temperature for 4 hours. The catalyst was removed by filtration, washed with methanol (500 ml). Both filtrates were combined and then evaporated to dryness. The residue was dissolved in dichloromethane and the solution was filtered through a short and wide column with silica gel (100 g). The column was additionally washed with CH2CI2/Me0H (200 ml, 4:1). The filtrate and washings were combined and evaporated to small volume. The formed precipitate was filtered off to give 3-amino-6- chloro-pyridine-2-carboxamide (8.1 g). The final filtrate was evaporated to dryness and the residue purified by column chromatography on silica gel (30 g). The compound was eluted with the following solvent systems: CH2CI2 (200 ml), CH2CI2/Me0H 100:1 (200 ml). The appropriate fractions were evaporated in vacuo yielding an additional 1.15 g of S-amino-theta-chloro-pyridine^-carboxamide (total yield : 9.25 g, i.e. 90 %) which was characterised as follows:- M.p. 176-177C; – UV (MeOH): 212 (3.76), 256 (4.14), and 348 (3.76); and- elemental analysis: calculated for C6H6CIN3O (171.6): C 42.00 H 3.52 N 24.49. Found: C 42.42 H 3.54 H 24.11.

With the rapid development of chemical substances, we look forward to future research findings about 93683-65-9.

Reference:
Patent; 4 AZA Bioscience nv; WO2006/135993; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem