Reaction #2275678

ord-534c6977fef949d19a2de618a8069a9e

Reaction equation

CC(C)(C)CC(C)(C)NC(=O)c1ccc([N+](=O)[O-])cc1
4-Nitro-N-(tert-octyl)benzamide
[H][H]
hydrogen
→
CC(C)(C)CC(C)(C)NC(=O)c1ccc(N)cc1
4-amino-N-(tert-octyl)benzamide
Yield 76.1%

Reactants

CC(C)(C)CC(C)(C)NC(=O)c1ccc([N+](=O)[O-])cc1
4-Nitro-N-(tert-octyl)benzamide
[H][H]
hydrogen

Reagents

[Pd]
palladium-on-charcoal

Solvents

CCOC(C)=O
ethyl acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationAfter filtering
  2. 2
    Concentrationconcentrating the solvent

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08323624B2uspto-grants-2012_12