HCID 86727380, compound → 1-(5-Amino-2-fluoro-4-hydroxyphenyl)ethanone

HRID 519217Notes

Reaction equation

HRID 519217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]>CCO.C1COCC1.[Pd]>[NH2:9][C:5]1[C:6]([OH:8])=[CH:7][C:2]([F:1])=[C:3]([C:12](=[O:14])[CH3:13])[CH:4]=1

Participants

5

Reactant 1

HCID 86727380HCID 86727380, compound

Product 1

HCID 867273811-(5-Amino-2-fluoro-4-hydroxyphenyl)ethanoneYield 94.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-fluoro-4-hydroxy-5-nitro-phenyl)-ethanone (3 g, 15.7 mmol) in EtOH (30 mL) and THF (6 mL) was added 10% Pd/C (1.5 g, 1.4 mmol) and the reaction mixture was stirred at ambient temperature under an atmosphere of H2 for 2 h. The reaction mixture was filtered and the filtrate was evaporated in vacuo to give 1-(5-amino-2-fluoro-4-hydroxy-phenyl)-ethanone as black solid (2.5 g, 94%), which was used in the next step directly without further purification. 1H NMR (DMSO-d6, 400 MHz): δ 7.01 (d, J=8.0 Hz, 1H), 6.48 (d, J=12.4 Hz, 1H), 2.39 (d, J=4.8 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-fa8feb08716c4a73ace7073ba0b228d2
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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