Ammonium Chloride → 4-Amino-3-(2,4-difluorophenylamino)benzonitrile

HRID 1087200Notes

Reaction equation

HRID 1087200 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]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[C:13]#[N:14].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:18][C:17]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[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 198177173-(2,4-Difluorophenylamino)-4-nitrobenzonitrile

Product 1

HCID 198177244-Amino-3-(2,4-difluorophenylamino)benzonitrileYield 38.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-(2,4-difluorophenylamino)-4-nitrobenzonitrile (3.5 g), iron powder (3.5 g) and ammonium chloride (0.35 g) in ethanol (50 ml) and water (25 ml) was refluxed for 1 hour. The insoluble material was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with water, dried and evaporated to dryness. The residual oil (3 g) was purified by column chromatography on silica gel (100 g) eluting with a mixture of toluene and ethyl acetate to give a powder of 4-amino-3-(2,4-difluorophenylamino)benzonitrile (1.2 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationThe insoluble material was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residual oil (3 g) was purified by column chromatography on silica gel (100 g)
  9. washeluting with a mixture of toluene and ethyl acetate

Sources & evidence

ORD record
ord-36dc999588e54f398f9c761efe28eaa4
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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