Ethyl 3-fluoro-4-nitro-5-benzyloxyphenylacetate → Ethyl 4-amino-3-fluoro-5-hydroxyphenylacetate

HRID 1372653Notes

Reaction equation

HRID 1372653 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([O:11]CC2C=CC=CC=2)[C:7]=1[N+:8]([O-])=O>CCO.[C].[Pd]>[NH2:8][C:7]1[C:6]([OH:11])=[CH:5][C:4]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 17859018Ethyl 3-fluoro-4-nitro-5-benzyloxyphenylacetate

Product 1

HCID 17858886Ethyl 4-amino-3-fluoro-5-hydroxyphenylacetateYield 65%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Ethyl 3-fluoro-4-nitro-5-benzyloxyphenylacetate (1.54 g, 4.62 mmol) and 10% palladium-carbon (122 mg) were subjected to catalytic hydrogenation for 20 hours under normal pressure while stirring at room temperature in EtOH (20 ml). From the reaction mixture, the catalyst was filtered off. The filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate/hexane (1/2) eluate fractions, ethyl 4-amino-3-fluoro-5-hydroxyphenylacetate (639 mg, 65%) was obtained as a brown oil.

Workup

  1. filtrationFrom the reaction mixture, the catalyst was filtered off
  2. distillationThe filtrate was distilled under reduced pressure
  3. customto remove the solvent
  4. customThe residue was purified by chromatography on a silica gel column, whereby from ethyl acetate/hexane (1/2) eluate fractions

Sources & evidence

ORD record
ord-a4d9337bdb0b4fd6a7898fdd2254505f
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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