Methyl 4-chloro-2-[(3-chloropropyl)amino]-3-nitrobenzoate → Methyl 3-amino-4-chloro-2-[(3-chloropropyl)amino]benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-chloro-2-[(3-chloropropyl)amino]-3-nitrobenzoate (275 mg, 0.895) and Fe (150 mg, 2.69 mmol) in AcOH (2.8 mL) was stirred at 80° C. for 1 h. AcOH (2.8 mL) and Fe (350 mg, 6.27) were added to the reaction mixture at room temperature, and the resultant mixture was stirred at 80° C. for 30 min, filtered through Celite and concentrated in vacuo. After water was added to the residue, the resultant mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on NH silica gel eluting with a 3% ethyl acetate/n-hexane mixture to afford a yellow oil (201 mg, 0.725 mmol, 81%).

Provenance & Evidence