Ammonium Chloride → 5,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamine

HRID 1176847Notes

Reaction equation

HRID 1176847 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([N+:11]([O-])=O)[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22].[Cl-].[NH4+]>[Fe].C(OCC)(=O)C>[F:8][C:7]1[C:2]([F:1])=[C:3]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=2[F:22])[C:4]([NH2:11])=[C:5]([O:9][CH3:10])[CH:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 593863122,3-Difluoro-N-(2-fluoro-4-iodophenyl)-5-methoxy-6-nitroaniline

Product 1

HCID 532609665,6-difluoro-N1-(2-fluoro-4-iodophenyl)-3-methoxybenzene-1,2-diamineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2,3-difluoro-5-methoxy-6-nitro-phenyl)-(2-fluoro-4-iodo-phenyl)-amine (0.57 gm, 1.34 mmol) ethanol (20 ml), ammonium chloride (1.18 gm, 20.16 mmol) and iron powder (1.15 gm, 21.44 mmol) were added. This reaction mixture was kept stirring at reflux for 16 hours. The reaction mixture was allowed to cool and was filtered over celite and concentrated to dryness. The residue obtained was taken into ethyl acetate and was washed with water. The organic layer was dried over sodium sulfate and further purified by crystallization from ethanol to provide an off-white solid (0.47 gm, yield: 90.3%).

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureto cool
  3. filtrationwas filtered over celite and
  4. concentrationconcentrated to dryness
  5. customThe residue obtained
  6. washwas washed with water
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customfurther purified by crystallization from ethanol

Sources & evidence

ORD record
ord-8ac55b51d5b2495a8be88dab3d51c7d8
Source dataset
uspto-grants-2010_11
Patent number
US07842836B2

Reaction notes

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