(E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester → Tert-butyl 3-(4-amino-3-fluorophenyl)propanoate

HRID 1678689Notes

Reaction equation

HRID 1678689 reaction equation
[C:1]([O:5][C:6](=[O:19])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([F:18])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66905416(E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester

Product 1

HCID 66905628Tert-butyl 3-(4-amino-3-fluorophenyl)propanoateYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-3-(3-fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester (804 mg, 3.01 mmol) in ethyl acetate (10 ml) was hydrogenated on 10% palladium on charcoal for 30 min at 1.5 bar. The suspension was filtered, the filter cake washed with ethyl acetate and the filtrate evaporated and dried under high vacuum to give the product as light brown solid (713 mg, 3 mmol; 99%). This material was pure enough for the next step. MS: m/e=240.0 [M+H+].

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter cake washed with ethyl acetate
  3. customthe filtrate evaporated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-c8269afe9235414fba1b306c988bdd23
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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