Ethanol → (2-Amino-3-chlorophenyl)amine

HRID 1532604Notes

Reaction equation

HRID 1532604 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:3]=1[NH2:4].C(O)C.[H][H]>O.[Ni]>[Cl:1][C:2]1[C:3]([NH2:4])=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 698552-Chloro-6-nitroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 3462489(2-Amino-3-chlorophenyl)amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

2-Chloro-6-nitroaniline (14.10 g, 81.71 mmol), Raney-nickel (5.02 g of a 50% slurry in water), and ethanol (200 mL) were combined in an autoclave which was pressurized to 15 psig with hydrogen. The resulting mixture was allowed to stir overnight at RT. The mixture was then filtered through a pad of celite, which was subsequently washed with several portions of methanol, and the solvents were removed by rotary evaporation to afford 10.43 g (89%) of a viscous, brown oil, which darkened upon standing. MS (EI): m/z 143.1 (M+H).

Workup

  1. filtrationThe mixture was then filtered through a pad of celite, which
  2. washwas subsequently washed with several portions of methanol
  3. customthe solvents were removed by rotary evaporation
  4. customto afford 10.43 g (89%) of a viscous, brown oil, which

Sources & evidence

ORD record
ord-b7a037e9861e4b48b0e8d81ff0952ed5
Source dataset
uspto-grants-2001_03
Patent number
US06204249B1

Reaction notes

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