Ammonium Hydroxide → 3,4-Dichlorophenethylamine

HRID 420793Notes

Reaction equation

HRID 420793 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH4+].[OH-]>C(O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 2179583,4-DichlorophenethylamineYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 3,4-dichlorophenylacetonitrile (3.001 g, 16.13 mmol) in ethanol (33 mL) and 29% NH4OH (6.7 ml, 611.2 mg, 17.44 mmol) in the presence of Raney Ni (333 mg, 3.887 mmol) was stirred vigorously under H2 (1 atm) for 6 h. The reaction mixture was filtered through Celite then the filtrate was concentrated under reduced pressure to give 2-(3,4-dichlorophenyl)ethylamine (2.82 g, 92%) as a pale yellow oil. LC/MS ((10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)), m/z: M+1 obs=190.3; tr=0.80 min.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ca89cf11e7a4913959070f8327a595d
Source dataset
uspto-grants-2012_01
Patent number
US08097636B2

Reaction notes

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