Ethyl Acetate → 2-(4-Amino-3-fluoro-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 889388Notes

Reaction equation

HRID 889388 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].[H][H].C(OCC)(=O)C>[Pd].C(O)C>[CH2:1]([O:3][C:4](=[O:19])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([F:18])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 671311902-(3-Fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 671309762-(4-Amino-3-fluoro-phenoxy)-2-methyl-propionic acid ethyl esterYield 127.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (200 mg) was added to a solution of 2-(3-fluoro-4-nitro-phenoxy)-2-methyl-propionic acid ethyl ester (1.15 g, 4 mmol) in ethanol (20 ml). The suspension was hydrogenated at a hydrogen gas pressure of 1.7 bar for 8 h at ambient temperature. Ethyl acetate was added (100 ml), the solid was filtered off and the filtrate was brought to dryness under reduced pressure to give the title compound (1.23 g, quant.) which was used in the next step without further purification.

Workup

  1. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-29fdff4180c44d04a2fa9ba52ba5d2e7
Source dataset
uspto-grants-2012_08
Patent number
US08252826B2

Reaction notes

Loading…