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

Temperature

80 °C

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%).

1. filtrationfiltered through Celite
2. concentrationconcentrated in vacuo
3. additionAfter water was added to the residue
4. extractionthe resultant mixture was extracted with ethyl acetate
5. washThe extract was washed with aqueous sodium hydrogen carbonate and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash column chromatography on NH silica gel eluting with a 3% ethyl acetate/n-hexane mixture

ORD record

ord-d77338f9bb65450eb75dbeb317584356

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901141B2