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

HRID 471447Notes

Reaction equation

HRID 471447 reaction equation
[N+:1]([C:4]1[C:13]([CH3:14])=[CH:12][C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH3:15])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:5]([CH3:15])=[CH:6][C:7]([C:8]([NH:10][CH3:11])=[O:9])=[CH:12][C:13]=1[CH3:14]

Participants

4

Reactant 1

HCID 86697180N,3,5-Trimethyl-4-nitrobenzamide

Product 1

HCID 668742744-amino-N,3,5-trimethylbenzamideYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Nitro-3,5,N-trimethyl-benzamide (1.0 g, 4.8 mmol) is suspended in methanol (10 mL) and hydrogenated at 3 bar for 3 hours using 10% Palladium on activated carbon (100 mg) as the catalyst. The mixture is filtered through celite and the solvent removed under vacuum to give the title compound (Yield 850 mg).

Workup

  1. filtrationThe mixture is filtered through celite
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-4c035677036649519800a4b9ee9957a0
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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