Acetaldehyde → HCID 86632907, compound

Participants

Reaction Steps

To a mixture of 4-fluoro-3-nitrobenzene-1,2-diamine (800 mg, 4.67 mmol), sodium acetoxyborohydride (5.94 g, 28.0 mmol), methanol (9 mL) and acetic acid (2.3 mL) was added acetoaldehyde (90%, 1.75 mL, 28.1 mmol) at 0° C. After the resultant mixture was stirred at 0° C. for 30 min, the mixture was diluted with aqueous sodium hydrogen carbonate and aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10 ethyl acetate/n-hexane mixture to give the title compound as a red oil (942 mg, 4.15 mmol, 89%).

Provenance & Evidence