Water → tert-Butyl 2-amino-5-methylbenzoate

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:15]C(=O)C(F)(F)F)=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[BH4-].[Na+].O>C(O)C>[NH2:15][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

Procedure

To a suspension of tert-butyl 5-methyl-2-(2,2,2-trifluoroacetamido)benzoate (19.78 mmol, 6.0 g) in ethanol (19 ml) was cooled with a water-iced bath. NaBH4 (39.57 mmol, 1.50 g) was added in portions and the mixture was stirred at room temperature for 3 hours. Water (40 ml) was added slowly and evaporated. The solid was dissolved with CHCl3 and washed with water and brine. The organic phase was evaporated affording 3.73 g (yield 91%) of the expected product.