Sodium Carbonate → 2-(4-Aminophenyl)-2-methylpropanenitrile

HRID 450043Notes

Reaction equation

HRID 450043 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4].C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 8236152-Methyl-2-(4-nitrophenyl)propanenitrile

Product 1

HCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-methyl-2-(4-nitro-phenyl)-propionitrile was dissolved in ethyl acetate (20 ml) and treated with stannous chloride dihydrate (3.52 g, 15.86 mmol). After stirring overnight at room temperature, the reaction mixture was basified with aqueous sodium carbonate. The organic layer was separated, washed with water, dried and concentrated to oil. The crude compound was purified by column chromatography over silica gel using ethyl acetate/pet ether (1:9) as eluent to give 2-(4-aminophenyl)-2-methyl propionitrile (0.45 g, 89%) as oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated to oil
  5. customThe crude compound was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-b2f4103661f74422b3ec80169c3185f3
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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