Water → chloromaleic acid N-[2-(2-methoxyphenyl)-ethyl]-imide

Reaction equation

[Cl:1][C:2]1[C:3]([O:5][C:6](=[O:8])[CH:7]=1)=[O:4].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][NH2:19].O>C(O)(=O)C>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18][N:19]=[C:3]([OH:4])/[C:2](/[Cl:1])=[CH:7]\[C:6]([OH:5])=[O:8]

Participants

Procedure

13.25 g (0.1 mol) of chloromaleic anhydride and 15.2 g (0.1 mol) of 2-(2-methoxyphenyl)-ethylamine are heated to the boiling point in 100 ml of glacial acetic acid for 4 hours. 100 ml of water are then added and the oil which has precipitated is extracted with methylene chloride. The methylene chloride phase is separated off, washed with water, dried and evaporated. The oil which remains crystallizes. 20.8 g (78% of theory) of chloromaleic acid N-[2-(2-methoxyphenyl)-ethyl]-imide are obtained.