Pyridine → N-(5-methylpyridin-2-yl)-2-nitrobenzamide

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.N1C=CC=CC=1.[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21])([O-:17])=[O:16]>ClCCl>[N+:15]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1)=[O:21])([O-:17])=[O:16]

Participants

Procedure

To a stirring solution of 2-amino-5-methylpyridine (3.1 g, 29 mmol) in dichloromethane (200 mL) was added pyridine (7.3 mL, 90 mmol) followed by 2-nitrobenzoyl chloride (5.7 g, 30 mmol). After 4 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate (500 mL) and water (250 mL). The organic phase was separated and washed with water, brine, dried (MgSO4) and filtered, and then concentrated in vacuo to a volume of about 100 mL (precipitate observed). The mixture was then sonicated and allowed to stand overnight then filtered. The collected solid was then washed with diethyl ether, filtered and dried under vacuum to give 3.9 g (52%) of the title compound.