Acetic Acid → HCID 118117479, compound

Participants

Reaction Steps

A mixture of aniline (128 mg, 1.38 mmol), methyl 6-formylpyridine-2-carboxylate (217 mg, 1.31 mmol) and acetic acid (75 μL, 1.31 mmol) in dichloromethane (10 mL) was stirred at room temperature for 24 h. After this time, sodium triacetoxyborohydride (695 mg, 3.28 mmol) was added in one portion and the resulting mixture was stirred at room temperature for 18 h. The reaction was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound (310 mg, 97%) as yellow oil.

Provenance & Evidence