O-ethoxycarbonyl-2,3,4-trifluoro-5-nitrophenol → 5-amino-O-ethoxycarbonyl-2,3,4-trifluorophenol

HRID 1736247Notes

Reaction equation

HRID 1736247 reaction equation
[CH2:1]([O:3][C:4]([O:6][C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([F:16])=[C:9]([F:17])[C:8]=1[F:18])=[O:5])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:13][C:11]1[C:10]([F:16])=[C:9]([F:17])[C:8]([F:18])=[C:7]([O:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:12]=1

Participants

5

Reactant 2

HCID 86749656O-ethoxycarbonyl-2,3,4-trifluoro-5-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 867496575-amino-O-ethoxycarbonyl-2,3,4-trifluorophenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.43 g (5.40 mmol) of the above O-ethoxycarbonyl-2,3,4-trifluoro-5-nitrophenol was dissolved in 20 mL of ethyl acetate under argon atmosphere, 200 mg of 10% palladium/carbon was added thereto, the gaseous phase in the reaction vessel was substituted with hydrogen and the mixture was stirred at room temperature for 4 hours. The reaction solution was filtered and the solvent was distilled off under reduced pressure to give 1.27 g of 5-amino-O-ethoxycarbonyl-2,3,4-trifluorophenol (yield: 100%).

Workup

  1. filtrationThe reaction solution was filtered
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dd3644305068464686ea4d749b293b1d
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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