Acetamide, N-ethyl-N-(4-nitrophenyl)- → Acetamide, N-(4-aminophenyl)-N-ethyl-

HRID 1356995Notes

Reaction equation

HRID 1356995 reaction equation
[C:1]([N:4]([CH2:14][CH3:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([N:4]([CH2:14][CH3:15])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 74583Acetamide, N-ethyl-N-(4-nitrophenyl)-

Product 1

HCID 74921Acetamide, N-(4-aminophenyl)-N-ethyl-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

N-acetyl-N-ethyl-4-nitroaniline (9a) (1.8 g, 8.64 mmol) is hydrogenated in THF (30 ml), over 10%Pd on carbon (100 mg) for 1.5 hours. The catalyst is removed by filtration and the solvent removed evaporation. The product crystalises on standing in hexane, and following filtration, is dried under vacuum; ES+ (M+1) 178.88.

Workup

  1. customfor 1.5 hours
  2. customThe catalyst is removed by filtration
  3. customthe solvent removed
  4. customevaporation
  5. customThe product crystalises
  6. filtrationfiltration
  7. customis dried under vacuum

Sources & evidence

ORD record
ord-e61e8923ca8d4396b3db6ca9e2d5bab2
Source dataset
uspto-grants-2003_07
Patent number
US06589950B1

Reaction notes

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