Ammonia → 4-Chloro-2-[imino(phenyl)methyl]-N-methylaniline

Reaction equation

[CH3:1][N:2]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C=O.[NH3:20]>[Cl-].[Zn+2].[Cl-].CO>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([NH:2][CH3:1])=[C:6]([CH:7]=1)[C:12](=[NH:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Procedure

A mixture of 41.1 g (0.15 mole) of N-methyl-N-(2-benzoyl-4-chlorophenyl)formamide, 90 ml methanol, 90 g anhydrous ammonia, and 0.5 g zinc chloride was heated in a sealed 360 ml Hastelloy® tube at 150° for 15 hr. and then cooled and vented. The solid portion of the residue was collected on a filter and recrystallized from methanol to give 27.8 g (76%) of 5-chloro-2-methylaminobenzophenone imine as long yellow needles: mp 93°-95°; 1H nmr (CDCl3) δ 2.92 ppm (d, J = 5.5 Hz, 3H), 6.65 ppm (d, J = 9 Hz, 1H) 7.4 ppm (m, 7H) and 9.4 ppm (broad, 2NH).