Acetone → N~1~-(4-Chloro-2-fluorophenyl)cyclohex-1-ene-1,2-dicarboxamide
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14](=[O:15])[CH:13]2[CH2:16][CH2:17][CH2:18][C:11](=[CH:12]2)C1=O.[NH3:20].C[C:22](C)=[O:23]>>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:14](=[O:15])[C:13]1[CH2:12][CH2:11][CH2:18][CH2:17][C:16]=1[C:22]([NH2:20])=[O:23]Participants
4
Procedure
In acetone (100 ml) was dissolved N-(2-fluoro-4-chlorophenyl)-3,4,5,6-tetrahydroisophthalimide (22.5 g), and under cooling, 25% aqueous ammonia (5.8 g) was added dropwise over a period of about one minute, the temperature of the system being maintained below 25° C. The mixture was further stirred for 30 minutes, after which the precipitate was recovered by filtration and washed with a small amount of cold acetone. Yield 22.2 g; m.p. 150°-151° C.