Ammonium Chloride → HCID 21450608, compound

HRID 242792Notes

Reaction equation

HRID 242792 reaction equation
[Cl:1][C:2]1[C:3]([N+:15]([O-])=O)=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-]>CO.O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[NH2:15]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 44126964(3-Chloro-2-nitrophenyl)phenylamine

Product 1

HCID 21450608HCID 21450608, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of (3-chloro-2-nitrophenyl)phenylamine (0.0109 mol) in MeOH (150 mL) and water (50 mL) were added NH4Cl (3.51 g, 0.0656 mol) and iron powder (2.45 g, 0.0438 mol) and the reaction mixture was heated to reflux temperature for 3 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 affording 3-Chloro-N1-phenylbenzene-1,2-diamine as a light brown solid (2.61 g, quantitative). LCMS: RT 3.72 min [M+H]+ 219.0

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux temperature for 3 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

Sources & evidence

ORD record
ord-4bc76dde30b347eea1b1d79d51a0451b
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…