N,N,3,5-Tetramethyl-4-nitrobenzamide → 4-amino-N,N,3,5-tetramethylbenzamide

HRID 237516Notes

Reaction equation

HRID 237516 reaction equation
[CH3:1][N:2]([CH3:16])[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:8]([CH3:10])=[CH:9][C:4]([C:3]([N:2]([CH3:16])[CH3:1])=[O:15])=[CH:5][C:6]=1[CH3:14]

Participants

5

Reactant 2

HCID 86697177N,N,3,5-Tetramethyl-4-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 668745564-amino-N,N,3,5-tetramethylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Palladium on carbon (100 mg) is added to a solution of N,N,3,5-tetramethyl-4-nitrobenzamide (1 g) in methanol (10 mL) and the mixture is hydrogenated for 3 hours under 2 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: 1 g; LC (method 20): tR=2.75 min; Mass spectrum (ESI+): m/z=193 [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-a000bc74508e4ab981e6d592631e2633
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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