2-Methyl-5-nitrobenzonitrile → 5-Amino-2-methylbenzonitrile

HRID 1921318Notes

Reaction equation

HRID 1921318 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5]>[Pd].C(O)C>[NH2:10][C:7]1[CH:8]=[CH:9][C:2]([CH3:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

4

Reactant 1

HCID 3501432-Methyl-5-nitrobenzonitrile

Product 1

HCID 27353655-Amino-2-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-5-nitrobenzonitrile (25.0 g, 154 mmol), 10% palladium on charcoal (2.5 g) ethyl acetate (150 mL) and ethanol (150 mL) is stirred under an atmosphere of hydrogen. The catalyst is removed by filtration through a pad of celite and the filtrate is concentrated to give 5-amino-2-methylbenzonitrile (also see, Scholz, D. et al. J. Med. Chem., 41, 1050-1059 (1998)) (19.6 g, 96%) as a tan solid. MS: m/e=133 (M+H).

Workup

  1. customThe catalyst is removed by filtration through a pad of celite
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-42de3c32b31943e397a9f70236c40e74
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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