2-(2,3-Dimethylphenyl)acetonitrile → 2,3-Dimethylbenzeneethanamine

HRID 1866533Notes

Reaction equation

HRID 1866533 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[H][H]>N.[Ni]>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH2:11]

Participants

5

Reactant 2

HCID 101300272-(2,3-Dimethylphenyl)acetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 223795192,3-DimethylbenzeneethanamineYield 66%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A mixture of 2,3-dimethylphenylacetonitrile (J. Org Chem, 51(26), 5157-60; 1986), (190 mg, 1.31 mmol) and Raney® nickel (100 mg) in 2M methanolic ammonia (5 mL) was stirred under 50 psi of hydrogen gas for 4 days. The mixture was then filtered through Arbocel® and concentrated in vacuo to afford the title compound as a solid in 66% yield, 130 mg. 1H NMR (400 MHz, CDCl3) δ: 7.02-6.94 (3H, m), 2.26-2.13 (10H, m) ppm; LRMS ESI m/z 150 [M+H]+

Workup

  1. filtrationThe mixture was then filtered through Arbocel®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f189dc5ef5ca42ddb45a98f406b905fb
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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