Acetic Acid → (2-Amino-3-chlorophenyl)amine

HRID 1012086Notes

Reaction equation

HRID 1012086 reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C(O)(=O)C>C(O)(C)C.O.[Ni]>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:4]([NH2:5])[C:3]=1[NH2:9]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 1010683-Chloro-2-nitroaniline

Product 1

HCID 3462489(2-Amino-3-chlorophenyl)amineYield 67%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

3-Chloro-2-nitro-aniline (0.345 g, 2 mmol) was dissolved in iso-propanol (10 ml) and water (2 ml). Catalytic acetic acid (0.1 ml) was added, followed by Raney nickel (0.02 g, as 50% slurry in H2O) under a flow of nitrogen. The reaction mixture was then shaken under an atmosphere of hydrogen at ambient temperature for 5 hours and the catalyst was removed by filtration under a nitrogen atmosphere. The filtrate was reduced in vacuo, partitioned between ethyl acetate and water, and the organic layer reduced in vacuo to give 3-chloro-benzene-1,2-diamine as a brown oil (0.190 g, 67%). (LC/MS: Rt 1.84, [M+H]+ 143.07).

Workup

  1. customthe catalyst was removed by filtration under a nitrogen atmosphere
  2. custompartitioned between ethyl acetate and water

Sources & evidence

ORD record
ord-587d67c77aa549998a2a52d287066c99
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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