反应详情

To a mixture of (2-chloro-6-nitrophenyl)phenylamine (676 mg, 2.72 mmol) in MeOH (45 mL) and water (15 mL) were added NH4Cl (872 mg, 16.31 mol) and iron powder (607 mg, 10.87 mmol) and the reaction mixture was heated to reflux temperature for 4 h. After cooling to RT, the solid was filtered through a pad of Celite® and washed with additional MeOH. The filtrate was concentrated in vacuo and then partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 50-100% DCM in cyclohexane). The product containing fractions were concentrated in vacuo affording 3-Chloro-N2-phenylbenzene-1,2-diamine as a pale orange solid (500 mg, 84%). LCMS: RT 3.45 min [M+H]+ 219.1.

1. temperaturethe reaction mixture was heated
2. temperatureto reflux temperature for 4 h
3. filtrationthe solid was filtered through a pad of Celite®
4. washwashed with additional MeOH
5. concentrationThe filtrate was concentrated in vacuo
6. custompartitioned between EtOAc and water
7. extractionThe aqueous phase was further extracted with EtOAc
8. washthe combined organic layers were washed with brine
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated in vacuo
11. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 50-100% DCM in cyclohexane)
12. additionThe product containing fractions
13. concentrationwere concentrated in vacuo