N,N-Dimethyl-4-nitro-benzamide → 4-Amino-N,N-dimethylbenzamide

HRID 517416Notes

Reaction equation

HRID 517416 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1>CO.[Pd]>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([N:2]([CH3:14])[CH3:1])=[O:13])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 138975N,N-Dimethyl-4-nitro-benzamide

Product 1

HCID 2355274-Amino-N,N-dimethylbenzamideYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N,N-dimethyl-4-nitro benzamide (23 g, 0.1185 mol) in MeOH (200 mL) was added Pd/C 10% (2.3 g) in portions and the Parr reaction vessel was purged with nitrogen for 10 min. The reaction vessel was fixed in Parr shaker at 60 psi pressure for 3 h. The reaction mixture was filtered through the Celite® pad and the filtrate was concentrated under reduced pressure to afford the title compound [18.0 g, 93%]; LC-MS (ESI): Calculated mass: 164.1; Observed mass: 165.2 [M+H]+ (RT: 0.17 min).

Workup

  1. customthe Parr reaction vessel
  2. customwas purged with nitrogen for 10 min
  3. filtrationThe reaction mixture was filtered through the Celite® pad
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-baaef54a803f4c94bc1589a68293a647
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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