Ethyl Acetate → 3,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamine

HRID 424003

Reaction equation

HRID 424003 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:15]([N+:16]([O-])=O)=[C:14]([F:19])[CH:13]=[C:12]([F:20])[C:11]=1[F:21].[Cl-].[NH4+].CCOC(C)=O>CCO.[Fe]>[F:21][C:11]1[C:12]([F:20])=[CH:13][C:14]([F:19])=[C:15]([NH2:16])[C:10]=1[NH:9][C:3]1[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 574300722,3,5-trifluoro-N-(2-fluoro-4-iodophenyl)-6-nitroaniline

Product 1

HCID 593863433,5,6-trifluoro-N1-(2-fluoro-4-iodophenyl)benzene-1,2-diamineYield 66.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To the stirred solution of (2-fluoro-4-iodo-phenyl)-(2,3,5-trifluoro-6-nitro-phenyl)-amine 3 (5.2 gm, 12.62 mmol) in EtOH (200 ml), ammonium chloride (10.12 gm, 189.3 mmol) and iron powder (10.57 gm, 189.3 mmol) was added. This reaction mixture was kept stirring at reflux for 16 hours. Reaction mixture was allowed to cool and was filtered over celite and concentrated to dryness. The residue obtained was taken into EtOAc and was washed with water. The EtOAc layer was dried over sodium sulfate and further purified by crystallization from EtOH to provide off-white solid (3.2 gm, yield: 66.39%). M−H+: 381.1. 1H NMR (DMSO, 300 MHz): 5.0 (s, 2H); 6.2 (t, 1H); 7.2-7.3 (m, 2H); 7.45 (s, 1H); 7.5 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-4900108a9d1942c9bd23f96d841ca238
Source dataset
uspto-grants-2012_01
Patent number
US08101799B2

Linked notes

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