[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=C([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])C#N.[OH-:21].[Na+].Cl.[CH2:24]([OH:26])[CH3:25]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[C:25]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:24]([OH:21])=[O:26]A mixture of 3-(2,4-difluorophenylamino)-4-nitrobenzonitrile (6.9 g) and 24% sodium hydroxide solution (50 ml) in ethanol (50 ml) was refluxed for 2 hours. The mixture was poured into ice-water (400 ml) and acidified with hydrochloric acid. The precipitate was filtered and washed with water to give red brown needles of 3-(2,4-difluorophenylamino)-4-nitrobenzoic acid (7.1 g).
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