N,3,5-Trimethyl-4-nitrobenzamide → 4-amino-N,3,5-trimethylbenzamide

HRID 237519Notes

Reaction equation

HRID 237519 reaction equation
[CH3:1][NH:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-])=O)=[C:6]([CH3:14])[CH:5]=1.[H][H]>[Pd].CO>[NH2:11][C:7]1[C:6]([CH3:14])=[CH:5][C:4]([C:3]([NH:2][CH3:1])=[O:15])=[CH:9][C:8]=1[CH3:10]

Participants

5

Reactant 2

HCID 86697180N,3,5-Trimethyl-4-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 668742744-amino-N,3,5-trimethylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (100 mg) is added to a solution of N,3,5-trimethyl-4-nitrobenzamide (1 g) in methanol (10 mL) and the mixture is hydrogenated for 3 hours under 3 bar hydrogen pressure. Then the catalyst is filtered off and washed with methanol. The combined mother liquors are concentrated to give the title compound. Yield: 850 mg; LC (method 21): tR=6.02; Mass spectrum (ESI+): m/z=179 [M+H]+.

Workup

  1. filtrationThen the catalyst is filtered off
  2. washwashed with methanol
  3. concentrationThe combined mother liquors are concentrated

Sources & evidence

ORD record
ord-9faac96f7a6f422bb76c273f4b757674
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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