4-tert-butyl-N-(4-nitrophenyl)benzamide → N-(4-aminophenyl)-4-tert-butylbenzamide

HRID 846204Notes

Reaction equation

HRID 846204 reaction equation
[CH3:1][C:2]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3]>[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:21]=[CH:22][C:5]([C:2]([CH3:3])([CH3:1])[CH3:4])=[CH:6][CH:7]=2)=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 28498204-tert-butyl-N-(4-nitrophenyl)benzamide

Product 1

HCID 721125N-(4-aminophenyl)-4-tert-butylbenzamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4.5 g. (0.015 mol) 4-(1,1-Dimethylethyl)-N-(4-nitrophenyl)-benzamide (Example 15 ) are hydrogenated at normal pressure and ambient temperature in the presence of 0.5 g. 10% palladium on charcoal. After 30 minutes, the reaction mixture is filtered and the filtrate is evaporated in a vacuum. The residue is digested with ligroin and filtered off with suction. There are obtained 3.4 g. (85% of theory) of the title compound; m.p. 111°-113° C.

Workup

  1. customare hydrogenated at normal pressure and ambient temperature in the presence of 0.5 g
  2. filtrationthe reaction mixture is filtered
  3. customthe filtrate is evaporated in a vacuum
  4. filtrationfiltered off with suction
  5. customThere are obtained 3.4 g

Sources & evidence

ORD record
ord-089ce2eaaec84d91a810a69bce9f3a96
Source dataset
uspto-grants-1992_08
Patent number
US05135949

Reaction notes

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