N,N-dimethyl-2-nitrobenzamide → 2-Amino-N,N-dimethylbenzamide

HRID 2294140Notes

Reaction equation

HRID 2294140 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-])=O>[Pd].C(O)C>[NH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([N:2]([CH3:14])[CH3:1])=[O:13]

Participants

4

Reactant 1

HCID 3261775N,N-dimethyl-2-nitrobenzamide

Product 1

HCID 47781752-Amino-N,N-dimethylbenzamideYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N,N-dimethyl-2-nitrobenzamide (4.76 g, 24.5 mmol) and 10% palladium on carbon (470 mg) in 100 mL of ethanol was stirred under hydrogen at atmospheric pressure for approximately 12 hours. The mixture was filtered and concentrated to dryness to give 2-amino-N,N-dimethylbenzamide (4 g, 24.2 mmol), m.p. 53°-54° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f6451c774b1749d49a417ccd75964742
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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