4-Methyl-3-nitrobenzonitrile → 3-Amino-4-methylbenzonitrile

HRID 1294447Notes

Reaction equation

HRID 1294447 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1)#[N:2].[H][H]>[Pd].C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([NH2:10])[CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 5893334-Methyl-3-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 70164283-Amino-4-methylbenzonitrileYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a reaction vessel was charged 4-cyano-2-nitrotoluene (12) (300 g) and ethanol, and 10% palladium/carbon (9.5 g) was added to this and a hydrogen catalytic reduction reaction was conducted at room temperature. When absorption of hydrogen disappeared, palladium/carbon was removed by filtration, then, the solvent was distilled off from filtrate, to obtain 4-cyano-2-aminotoluene (13) (132.5 g, yield from (11) is 98%).

Workup

  1. additionwas added to this and
  2. customwas conducted at room temperature
  3. customWhen absorption of hydrogen
  4. custompalladium/carbon was removed by filtration
  5. distillationthe solvent was distilled off from filtrate

Sources & evidence

ORD record
ord-002ddf63cffd44f4b9656d9c8a6700e2
Source dataset
uspto-grants-2007_07
Patent number
US07241625B2

Reaction notes

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