N-Decyl-4-nitrobenzamide → 4-Amino-N-decylbenzamide

HRID 1757865Notes

Reaction equation

HRID 1757865 reaction equation
[CH2:1]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>[Pd].C1COCC1>[CH2:1]([NH:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 3414942N-Decyl-4-nitrobenzamide

Product 1

HCID 193889594-Amino-N-decylbenzamideYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8.05 g of 4-[(decylamino)carbonyl]nitrobenzene and 2.5 g of 10% palladium on carbon in 175 ml of THF was shaken under an initial hydrogen pressure of 54 psi in a Parr Hydrogenator for 17 hours. The catalyst was removed by filtration and the filtrate was concentrated to a solid which was triturated with hexane and filtered to give 6.88 g (95% yield, mp 117°-119°) of 4-[(decylamino)carbonyl]benzenamine.The structure was confirmed by the nmr spectrum.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to a solid which
  3. customwas triturated with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5f3ce0f9d8384ae9bcd638a2570fe5c2
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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