Ammonium Chloride → HCID 10378008, compound

HRID 1087196Notes

Reaction equation

HRID 1087196 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:11]=[C:12]([C:19](=[O:21])[CH3:20])[CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:16][C:15]1[CH:14]=[CH:13][C:12]([C:19](=[O:21])[CH3:20])=[CH:11][C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 19817727HCID 19817727, compound

Product 1

HCID 10378008HCID 10378008, compoundYield 22.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3'-(2,4-difluorophenylamino)-4'-nitroacetophenone (8.5 g), iron powder (8 g), and ammonium chloride (0.8 g) in ethanol (100 ml) and water (50 ml) was refluxed with stirring for 1 hour. The insoluble was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated. The residual oil was purified by column chromatography on silica gel (150 g) eluting with a mixture of toluene and ethyl acetate (20:1) to give a powder of 4'-amino-3'-(2,4-difluorophenylamino)acetophenone (1.7 g).

Workup

  1. temperaturewas refluxed
  2. filtrationThe insoluble was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residual oil was purified by column chromatography on silica gel (150 g)
  9. washeluting with a mixture of toluene and ethyl acetate (20:1)

Sources & evidence

ORD record
ord-c2a350ae95434463995e38821223028b
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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