Water → 4-Amino-N-(2,4,4-trimethylpentan-2-yl)benzamide

HRID 403092Notes

Reaction equation

HRID 403092 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.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

6

Reactant 3

HCID 962WaterHCID 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 was hydrogenated in a 500 ml hydrogenator in the presence of 4.8 g of palladium, 10% on charcoal with 50% water as the catalyst (hydrogen pressure: 8-10 bar) at a temperature of 70-75° C. for 1 hour and 15 minutes. After filtering, concentrating the solvent and vacuum drying, 20.4 g (yield: 76%) of 4-amino-N-(tert-octyl)benzamide were obtained in the form of a pale yellow powder and used as is in the next step.

Workup

  1. filtrationAfter filtering
  2. concentrationconcentrating the solvent and vacuum
  3. customdrying

Sources & evidence

ORD record
ord-cb686fcd11754082b423ddabd6c855d7
Source dataset
uspto-grants-2014_06
Patent number
US08747816B2

Reaction notes

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