4-Nitro-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamide → 4-amino-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamide

HRID 471442Notes

Reaction equation

HRID 471442 reaction equation
[N+:1]([C:4]1[C:17]([CH3:18])=[CH:16][C:7]([C:8]([NH:10][CH2:11][C:12]([OH:15])([CH3:14])[CH3:13])=[O:9])=[CH:6][C:5]=1[CH3:19])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[C:5]([CH3:19])=[CH:6][C:7]([C:8]([NH:10][CH2:11][C:12]([OH:15])([CH3:13])[CH3:14])=[O:9])=[CH:16][C:17]=1[CH3:18]

Participants

4

Reactant 1

HCID 867038834-Nitro-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamide

Product 1

HCID 867038844-amino-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamideYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Nitro-N-(2-hydroxy-2-methyl-propyl)-3,5-dimethyl-benzamide (1.2 g, 4.51 mmol) is suspended in methanol (10 mL) and hydrogenated at 3 bar for 3 hours using 10% palladium on activated carbon (120 mg) as the catalyst. The mixture is filtered through celite and the solvent removed under vacuum to give the title compound (Yield 900 mg).

Workup

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

Sources & evidence

ORD record
ord-67c5733925104d7ca320afd798f14b04
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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