Ammonium Chloride → 4-amino-2-fluoro-N-methoxy-N-methylbenzamide

HRID 13419Notes

Reaction equation

HRID 13419 reaction equation
[Cl-].[NH4+:2].[F:3][C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7]>CO.O.[Fe]>[NH2:2][C:14]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[C:4]([F:3])[CH:15]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 183575562-fluoro-N-methoxy-N-methylbenzamide

Product 1

HCID 231456994-amino-2-fluoro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

15.2 g of ammonium chloride and 8 g of iron powder were added to a suspension of 10.84 g of 2-fluoro-N-methoxy-N-methylbenzamide in 60 ml of methanol and 30 ml of water, and the reaction liquid was heated under reflux for 3 hours. The reaction liquid was filtered through Celite, and the solvent was evaporated away under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 1/2 to obtain the entitled compound as a brown oily substance.

Workup

  1. customthe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux for 3 hours
  4. customThe reaction liquid
  5. filtrationwas filtered through Celite
  6. customthe solvent was evaporated away under reduced pressure
  7. additionThe resulting residue was diluted with ethyl acetate
  8. washwashed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customThe solvent was evaporated away under reduced pressure
  11. customthe resulting residue was purified through silica gel column chromatography (
  12. customhexane/ethyl acetate=9/1 to 1/2 to obtain the entitled compound as a brown oily substance

Sources & evidence

ORD record
ord-5f7d2768bf7e4062b30e215939d2ca76
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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