4-Methyl-2-nitroaniline → 2-Nitro-4-toluonitrile

HRID 378328

Reaction equation

HRID 378328 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5](N)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C-:12]#[N:13].[Na+]>[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([C:12]#[N:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

4

Reactant 2

HCID 69784-Methyl-2-nitroanilineHCID 8929Sodium Cyanide

Product 1

HCID 962352-Nitro-4-toluonitrile

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

11.75 g (77.2 mmol) of 4-methyl-2-nitroaniline underwent a Sandmeyer reaction in a conventional process by diazotization and substitution with NaCN and CuSO4 to give 9.6 g of crude 4-methyl-2-nitrobenzonitrile. 1H-NMR (DMSO-d6, δ in ppm): 8.25 (1H), 8.05 (1H), 7.80 (1H), 2.50 (3H)

Sources & evidence

ORD record
ord-1b522b4234d046afb932a038441e9a2f
Source dataset
uspto-grants-2000_02
Patent number
US06030972

Linked notes

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