Acetaldehyde → HCID 68763137, compound

Participants

Reaction Steps

A solution of 3-[(2,6-diamino-4-fluorophenyl)amino]propan-1-ol (498 mg, 2.50 mmol) and methyl 2-(2,4-dichlorophenyl)-2-hydroxyethanimidoate hydrochloride (812 mg, 3.00 mmol) in ethanol (5 mL) was stirred for 12 h at room temperature. The reaction mixture was diluted with aqueous sodium hydrogen carbonate, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was dissolved in acetic acid (1.2 mL) and methanol (25 mL), and acetaldehyde (935 μL, 15.0 mmol) was added at 0° C. After 30 min, sodium triacetoxyborohydride (3.18 g, 15.0 mmol) was added. After 6 h, the reaction mixture was quenched with water, concentrated in vacuo, diluted with ethyl acetate, washed with aqueous sodium hydroxide (1 M) and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (192 mg, 0.436 mmol, 17%).

Provenance & Evidence