[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[C:6](Cl)[CH:5]=1)[CH3:2].C[O-].[Na+].[CH3:21][O:22]NC1C=CC=CC=1>CO>[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[C:6]([O:22][CH3:21])[CH:5]=1)[CH3:2]A solution of 14.0 g. (0.052 mole) of N-ethyl-3-chloro-6-nitro-4-trifluoromethylaniline and 16.98 g. (0.057 mole) of 18.23% methanolic sodium methoxide in 25 ml. of anhydrous methanol was sealed in a glass tube and heated at 119°C. for 88 hours. Removal of the solvent by distillation left a yellow solid residue which was triturated with hot chloroform. Filtration and evaporation of chloroform from the filtrate gave a crude solid residue. Crystallization of the residue from ethanol gave 12.4 g. of yellow crystalline product, m.p. 140.5° - 141.5°C. shown by its NMR spectrum to be the desired methoxyaniline.
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