Methanol → 4-Chloro-N~2~-phenylbenzene-1,2-diamine

Temperature

90 °C

To a mixture of (5-chloro-2-nitrophenyl)phenylamine (1.36 g, 5.47 mmol) in a 3:1 mixture of MeOH:water (120 mL) were added NH4Cl (1.76 g, 32.81 mmol) and iron powder (1.22 g, 21.88 mmol) and the reaction mixture heated at 90° C. for 2 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 the resulting residue partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane) to afford the title compound as a brown oil (980 mg, 82%). LCMS (Method C): RT 3.57 min [M+H]+ 219.0

1. temperatureAfter cooling to RT
2. filtrationthe solid was filtered through a pad of Celite®
3. washwashed with additional MeOH
4. concentrationThe filtrate was concentrated in vacuo
5. customthe resulting residue partitioned between EtOAc and water
6. extractionThe aqueous phase was further extracted with EtOAc
7. washthe combined organic fractions washed with brine
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane)

ORD record

ord-463aa16dfab54811a6b5984837417b8f

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2