Water → Methyl 4-(allylamino)-5-amino-3-fluoro-2-(2-fluoro-4-iodophenylamino)benzoate

HRID 558188Notes

Reaction equation

HRID 558188 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]([N+:15]([O-])=O)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=2[F:26])[C:6]=1[F:27])[CH:2]=[CH2:3].[Cl-].[NH4+].O>CO.O1CCOCC1.[Fe]>[CH2:1]([NH:4][C:5]1[C:14]([NH2:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=2[F:26])[C:6]=1[F:27])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58781109Methyl 4-(allylamino)-3-fluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoate

Product 1

HCID 58781154Methyl 4-(allylamino)-5-amino-3-fluoro-2-(2-fluoro-4-iodophenylamino)benzoate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A suspension of methyl 4-(allylamino)-3-fluoro-2-(2-fluoro-4-iodophenylamino)-5-nitrobenzoate and ammonium chloride (4.42 g, 79 mmoles) in a mixture of MeOH (20 ml) and dioxane (20 ml) is heated until it became a clear solution. Iron powder (4.42 g, 79 mmoles) is added and the resulting mixture is heated under reflux overnight. Water is added and the reaction mixture is filtered through celite. The solvent is removed under reduced pressure and the crude material is purified by flash chromatography to give the title compound.

Workup

  1. temperatureis heated until it
  2. temperaturethe resulting mixture is heated
  3. temperatureunder reflux overnight
  4. filtrationthe reaction mixture is filtered through celite
  5. customThe solvent is removed under reduced pressure
  6. customthe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-057400bfbbda490aae1eedc86327b0ad
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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