4-Nitro-N-(tert-octyl)benzamide → 4-Amino-N-(2,4,4-trimethylpentan-2-yl)benzamide

HRID 2188496Notes

Reaction equation

HRID 2188496 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:12])=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:12])[CH3:13])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6980294-Nitro-N-(tert-octyl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 437127994-Amino-N-(2,4,4-trimethylpentan-2-yl)benzamideYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitro-N-(tert-octyl)benzamide (30 g, 0.108 mol) dissolved in 200 ml of ethyl acetate is hydrogenated for 1 hour 15 minutes at a temperature of 70-75° C. in a 500 ml hydrogenator in the presence of 4.8 g of 10% palladium-on-charcoal comprising 50% water as catalyst (hydrogen pressure: 8-10 bar). After filtering, concentrating the solvent and drying under vacuum, 20.4 g (Yield: 76%) of 4-amino-N-(tert-octyl)benzamide are obtained in the form of a pale yellow powder which is used as is in the following stage.

Workup

  1. filtrationAfter filtering
  2. concentrationconcentrating the solvent

Sources & evidence

ORD record
ord-534c6977fef949d19a2de618a8069a9e
Source dataset
uspto-grants-2012_12
Patent number
US08323624B2

Reaction notes

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