Methanol → Ethyl 4-(2-amino-phenylamino)-2-fluoro-benzoate

HRID 1792480Notes

Reaction equation

HRID 1792480 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Cl-].[NH4+].CO>[Fe].O>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:11]1[CH:10]=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[CH:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 22032336Ethyl 2-fluoro-4-(2-nitrophenylamino)benzoate

Product 1

HCID 22031117Ethyl 4-(2-amino-phenylamino)-2-fluoro-benzoateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

200 mg ethyl 2-fluoro-4-(2-nitrophenylamino)benzoate (compound in Production Example 331), 180 mg iron powder, 350 mg ammonium chloride and 8 mL solution mixture of methanol and water (5:3) were stirred at 100° C. for 1 hour. Insolubles were filtered off with Celite, and water was added to the filtrate which was then extracted with dichloromethane. The extract was purified by NH silica gel chromatography (ethyl acetate), to give 179 mg of the title compound as pale brown crystals.

Workup

  1. filtrationInsolubles were filtered off with Celite, and water
  2. additionwas added to the filtrate which
  3. extractionwas then extracted with dichloromethane
  4. customThe extract was purified by NH silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bbef1b1f3ba844cbbbb945a5c679fabc
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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