2,5-Dimethyl-4-methoxyphenylacetonitrile → Ammonia

HRID 1866532Notes

Reaction equation

HRID 1866532 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][C:11]#[N:12])=[C:5]([CH3:13])[CH:4]=1.[H][H]>N.[Ni]>[NH3:12].[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH2:10][CH2:11][NH2:12])=[C:5]([CH3:13])[CH:4]=1

Participants

6

Reactant 2

HCID 5948952,5-Dimethyl-4-methoxyphenylacetonitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 222AmmoniaHCID 23544174HCID 23544174, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A mixture of (4-methoxy-2,5-dimethyl-phenyl)-acetonitrile (200 mg, 1.14 mmol) and Raney® nickel (50 mg) in 2M methanolic ammonia (10 mL) was stirred under 60 psi of hydrogen gas at room temperature for 18 hours. Tlc analysis showed that not all of the starting material had been consumed and so further Raney® nickel (50 mg) in 2M methanolic ammonia (10 mL) was added. The reaction mixture was stirred under 60 psi of hydrogen gas for an additional 18 hours at room temperature and was then filtered through Arbocel®. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 90:10:1 to afford the title product as a pale brown solid in 38% yield, 98 mg. 1H NMR (400 MHz, CDCl3) δ: 6.87 (1H, s), 6.68 (1H, s), 3.77 (3H, s), 2.80 (2H, m), 2.69 (2H, m), 2.28 (3H, s), 2.10 (3H, s) ppm; LRMS APCI m/z 180 [M+H]+

Workup

  1. customhad been consumed
  2. additionso further Raney® nickel (50 mg) in 2M methanolic ammonia (10 mL) was added
  3. filtrationwas then filtered through Arbocel®
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-a630a9658e384a25bb766831a4aa5a61
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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