2-amino-4-fluoro-N,N-dimethyl-5-phenylmethoxybenzamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-benzyloxy-4-fluoro-N,N-dimethyl-2-nitrobenzamide (1.06 g) in THF (3 mL) were added ethanol (12 mL) and water (1.5 mL), and to the solution were added ammonium chloride (893 mg) and reduced iron (933 mg). The resultant mixture was heated under reflux for 2 hours, allowed to stand for cooling to room temperature, and filtered through a Celite. The filtrate was concentrated and the residue was diluted with ethyl acetate. The extract was washed with successively with saturated aqueous sodium bicarbonate, water, and saturated brine, dried over sodium sulfate, and concentrated to give 2-amino-5-benzyloxy-4-fluoro-N,N-dimethylbenzamide (984 mg) as a crude product. under reflux for 2 hours filtered through a Celite The filtrate was concentrated the residue was diluted with ethyl acetate The extract was washed with successively with saturated aqueous sodium bicarbonate, water, and saturated brine dried over sodium sulfate concentrated