Ammonium Chloride → 1-(3-Amino-4-Methylphenyl)Ethanone

HRID 1712891Notes

Reaction equation

HRID 1712891 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-])=O.[NH4+].[Cl-]>C(O)C.O.[Fe]>[NH2:11][C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 792463'-Nitro-4'-methylacetophenone

Product 1

HCID 3429141-(3-Amino-4-Methylphenyl)EthanoneYield 89.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(4-methyl-3-nitrophenyl)ethanone (5.37 g, 30 mmol), iron powder (8.4 g, 150 mmol) and NH4Cl (1.62 g, 30 mmol) in ethanol (100 mL) and water (10 mL) was heated at 80° C. overnight. The mixture was then heated at 110° C. for 5 hours and allowed to cool to room temperature. The resulting suspension was filtered and the filter cake was washed with ethanol. The filtrate was concentrated and the residue was dissolved in ethanol and filtered. The filtrate was concentrated to give 4 g of the title compound as a yellow solid. MS(ESI(+)) m/e 149.8 (M+H)+.

Workup

  1. temperatureThe mixture was then heated at 110° C. for 5 hours
  2. temperatureto cool to room temperature
  3. filtrationThe resulting suspension was filtered
  4. washthe filter cake was washed with ethanol
  5. concentrationThe filtrate was concentrated
  6. dissolutionthe residue was dissolved in ethanol
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-102a050088294d7da144636186144569
Source dataset
uspto-grants-2010_09
Patent number
US07795248B2

Reaction notes

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