Water → N-(3-aminophenyl)pentanamide

HRID 441276Notes

Reaction equation

HRID 441276 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[NH:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])([O-])=O.O>[Fe].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[NH:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 962WaterHCID 531778HCID 531778, compound

Product 1

HCID 5138852N-(3-aminophenyl)pentanamideYield 98.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 177.6 g of m-nitrovaleranilide, 160 ml of water, 8 ml of 22° Be hydrochloric acid and 640 ml of 95% ethanol was refluxed and 480 g of iron powder were added with stirring over 30 minutes. Reflux was continued for 30 minutes with stirring and the mixture was filtered. The filtrate was concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8- 2 methylene chloride-acetone mixture gave 151 g of m-aminovaleranilide with a specific rotation nD20 = 1.541.

Workup

  1. temperaturewas refluxed
  2. temperatureReflux
  3. waitwas continued for 30 minutes
  4. stirringwith stirring
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customthe residue was chromatographed over silica gel
  8. washElution with an 8- 2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-ca9d615e62c84de4b4aad95201a98513
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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