Ammonium Hydroxide → 4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline

Participants

Reaction Conditions

Reaction Steps

To a slurry of 4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]nitrobenzene (3.55 g, 10.6 mmol) [prepared as in Example 2, Step (a)] in methanol (170 ml) and hydrochloric acid (50 ml, 1M) was added nickel boride (3.41 g, 26.6 mmol), and the mixture was stirred at 75° C. for 15 h. The reaction mixture was cooled, basified with ammonium hydroxide and the product was extracted into ethyl acetate. The organic phase was washed with water and dried over sodium sulfate. Evaporation of the solvent gave 4-[5-benzoyl-1,4-dimethyl-1H-pyrrol-2-ylmethyl]aniline (3.11 g, 96%) as a pale yellow solid.

Provenance & Evidence