4-Nitro-N,N-dipropylbenzamide → 4-Amino-N,N-dipropylbenzamide

HRID 2295484Notes

Reaction equation

HRID 2295484 reaction equation
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[CH2:2][CH3:3]>C(O)C.[Pd]>[CH2:16]([N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH2:17][CH3:18]

Participants

4

Reactant 1

HCID 3479374-Nitro-N,N-dipropylbenzamide

Product 1

HCID 166412874-Amino-N,N-dipropylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An amount of 44.3 gm (0.2 mol) of the p-nitrobenzoic acid dipropylamide from step (a) was dissolved in 500 ml of ethanol and, after addition of 5 gm of palladium active charcoal (5%), hydrogenated at 50° C. and 60 bar pressure. After filtration, evaporation of the ethanol solution, and recrystallization of the residue (34.1 gm) from ether, 26.7 gm of p-aminobenzoic acid dipropylamide with a melting point of 78°-79° C. were obtained.

Workup

  1. customhydrogenated at 50° C.
  2. filtrationAfter filtration, evaporation of the ethanol solution, and recrystallization of the residue (34.1 gm) from ether, 26.7 gm of p-aminobenzoic acid dipropylamide with a melting point of 78°-79° C.
  3. customwere obtained

Sources & evidence

ORD record
ord-cc6427ef0dab4823a447722b90747fcd
Source dataset
uspto-grants-1984_01
Patent number
US04425327

Reaction notes

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