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

HRID 234762Notes

Reaction equation

HRID 234762 reaction equation
[CH3:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([N+:10]([O-])=O)=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:10][C:5]1[CH:6]=[C:7]([C:2]([CH3:1])=[CH:3][CH:4]=1)[C:8]#[N:9]

Participants

5

Reactant 1

HCID 3501432-Methyl-5-nitrobenzonitrile

Product 1

HCID 27353655-Amino-2-methylbenzonitrile

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 8.11 g (50 mmol) of 6-methyl-3-nitrobenzonitrile and 0.81 g of 10% of palladium-on-charcoal in 50 ml of ethanol and 50 ml of ethyl acetate is hydrogenated under 2.9 bar for 1 hour. The catalyst is filtered off, the filtrate is concentrated and the residue is crystallised from ether/petroleum ether.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customthe residue is crystallised from ether/petroleum ether

Sources & evidence

ORD record
ord-9b4b736072184c109f8288734ea4def8
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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