[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[C:8](O)=[O:9].[BH4-].[Na+].B(F)(F)F.CCOCC>COCCOC>[CH3:1][N:2]([CH3:15])[C:3]1[CH:4]=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[C:7]([CH:11]=1)[CH2:8][OH:9]A solution of 189 g of 5-dimethylamino-2-nitrobenzoic acid in 1.5 l of 1,2-dimethoxyethane was treated with 52 g of sodium borohydride and then dropwise at 10° with a solution of 225 ml of boron trifluoride etherate in 500 ml of 1,2-dimethoxyethane. The mixture was then stirred at room temperature for 1 hour, cautiously poured into ice/water and the crude product was filtered. Recrystallization from ethyl acetate/hexane gave pure 5-dimethylamino-2-nitrobenzyl alcohol, m.p. 138°-139°.
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