Ammonium Chloride → 4-Ethynyl-3-aminobenzamide

Participants

Reaction Steps

5 g (26.3 mmol) 4-Ethynyl-3-nitrobenzamide (Compound XII-1) and 75 ml tetrahydrofuran were added into a 150 ml four-necked flask, mechanically stirred to dissolve, and added with 10 ml aqueous solution of 10 g (186.9 mmol) ammonium chloride, then 10 g (178.5 mmol) iron powder was added portionwise and reacted at room temperature for 4 hours until the reaction was completed. The mixture was filtrated, and the filter cake was washed with tetrahydrofuran. The filtrate was extracted with ethyl acetate and the organic phase was washed with water, dried over anhydrous sodium sulfate, decolorized with activated charcoal, filtered, and concentrated to precipitate a solid, which was filtrated and dried to obtain 4-ethynyl-3-aminobenzamide (Compound XI-1, gray solid), 2.4 g, yield 59.4%.

Provenance & Evidence