Category: 105166-53-8

Adding a certain compound to certain chemical reactions, such as: 105166-53-8, [2,2′-Bipyridin]-3-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Product Details of 105166-53-8, blongs to pyridine-derivatives compound. Product Details of 105166-53-8

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,105166-53-8, [2,2′-Bipyridin]-3-amine, and friends who are interested can also refer to it.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105166-53-8 , The common heterocyclic compound, 105166-53-8, name is [2,2′-Bipyridin]-3-amine, molecular formula is C10H9N3, 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.

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.(Z)-3-(2-(2,2?-bipyridin-3-yl)hydrazono)indolin-2-one (3), yellow solid (328 mg, 52%): 1H-NMR (600 MHz,DMSO): delta15.70 (s, 1H), 10.89 (s, 1H), 8.80 (d, J = 4.0 Hz, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.45 (dd, J = 8.4,1.3 Hz, 1H), 8.37 (dd, J = 4.3, 1.4 Hz, 1H), 8.04-7.98 (m, 1H), 7.62 (d, J = 7.4 Hz, 1H), 7.54-7.46 (m, 1H),7.25 (dd, J = 7.6, 6.7 Hz, 1H), 7.04 (t, J = 7.2 Hz, 1H), 6.92 (d, J = 7.7 Hz, 1H). 13C-NMR (151 MHz,DMSO) delta161.83, 156.74, 147.04, 142.28, 140.39, 139.61, 137.59, 137.13, 130.36, 128.95, 125.16, 123.13,121.90, 121.74, 121.61, 121.27, 119.08, 110.29. Elem. anal. calcd. for C18H13N5O, C 68.56, H 4.16, N 22.21.Found: C 68.48, H 4.09, N 21.88. IR (ATR) nu/cm-1: 3180, 3047, 1693, 1464, 1164, 798. m.p: 238-240 C.

The synthetic route of 105166-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 105166-53-8 , The common heterocyclic compound, 105166-53-8, name is [2,2′-Bipyridin]-3-amine, molecular formula is C10H9N3, 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.

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.(Z)-3-(2-(2,2?-bipyridin-3-yl)hydrazono)indolin-2-one (3), yellow solid (328 mg, 52%): 1H-NMR (600 MHz,DMSO): delta15.70 (s, 1H), 10.89 (s, 1H), 8.80 (d, J = 4.0 Hz, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.45 (dd, J = 8.4,1.3 Hz, 1H), 8.37 (dd, J = 4.3, 1.4 Hz, 1H), 8.04-7.98 (m, 1H), 7.62 (d, J = 7.4 Hz, 1H), 7.54-7.46 (m, 1H),7.25 (dd, J = 7.6, 6.7 Hz, 1H), 7.04 (t, J = 7.2 Hz, 1H), 6.92 (d, J = 7.7 Hz, 1H). 13C-NMR (151 MHz,DMSO) delta161.83, 156.74, 147.04, 142.28, 140.39, 139.61, 137.59, 137.13, 130.36, 128.95, 125.16, 123.13,121.90, 121.74, 121.61, 121.27, 119.08, 110.29. Elem. anal. calcd. for C18H13N5O, C 68.56, H 4.16, N 22.21.Found: C 68.48, H 4.09, N 21.88. IR (ATR) nu/cm-1: 3180, 3047, 1693, 1464, 1164, 798. m.p: 238-240 C.

The synthetic route of 105166-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem