Ethanol → 2-(4-Aminophenyl)acetamide

HRID 641061

Reaction equation

HRID 641061 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)([O-])=O.[NH2:10]N.[CH2:12]([OH:14])[CH3:13]>[Ni]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:13][C:12]([NH2:10])=[O:14])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 7416NitrobenzeneHCID 9321Hydrazine

Product 1

HCID 2380342-(4-Aminophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a suspension of Nitrobenzene (NB-2-A13, NB-2-A14 or NB-3-A16; 1.61 mmol) and Raney Ni (50 mg) in refluxing ethanol (10 mL) was added drop-wise anhydrous hydrazine (0.5 mL). After the addition was complete, the mixture was refluxed for an additional 20 minutes and then filtered through a pad of Celite. The Celite bed was washed with ethanol (100 mL) and the combined solution was evaporated under reduced pressure to provide pure 2-(4-aminophenyl)-acetamide (2-NB-2-A13, 2-NB-2-A14 or 2-NB-3-A16).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for an additional 20 minutes
  3. filtrationfiltered through a pad of Celite
  4. washThe Celite bed was washed with ethanol (100 mL)
  5. customthe combined solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bf03270b059c4d4cbdbf83f0b49e3002
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Linked notes

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