3-Chloro-2-methylaniline → N-(3-Chloro-2-methylphenyl)-3-nitropyridin-2-amine
Reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:11][C:12]1[C:13]([CH3:19])=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15]>>[Cl:11][C:12]1[C:13]([CH3:19])=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH:15][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
3
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 6.3 g. (0.04 mole) of 2-chloro-3-nitropyridine and 16.9 g. (0.12 mole) of 3-chloro-2-methylaniline was heated in an oil bath to 170° C. when the temperature spontaneously rose to 185° C. After an additional 10 minutes at 180° C., the mixture was cooled to 50° C. and extracted with a solution of 75 ml. of water and 25 ml. of acetic acid. The insolubles were collected, air dried, dissolved in methylene chloride, and the solution was dried over magnesium sulfate. The solution was concentrated to a small volume and diluted with 50 ml. of ether which caused crystallization of 6.6 g. of 2-(3-chloro-2-methylanilino)-3-nitropyridine, m.p. 134°-135° C.