3-(2,4-Difluorophenyl)acrylic Acid → 3-(2,4-difluorophenyl)propanoic Acid

HRID 2239794Notes

Reaction equation

HRID 2239794 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11]([OH:13])=[O:12]>CCO.O=[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 6035023-(2,4-Difluorophenyl)acrylic Acid

Product 1

HCID 49863953-(2,4-difluorophenyl)propanoic Acid

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.0 g (27.15 mmol) of 3-(2,4-difluorophenyl)acrylic acid in EtOH (50 mL) is hydrogenated over PtO2 catalyst under atmospheric pressure and stirred overnight at RT. After filtration to remove the catalyst, the filtrate is concentrated in vacuo to afford 3-(2,4-difluorophenyl)propanoic acid as a white solid: m.p. 104° C. 1H NMR (CDCl3, 400 MHz) δ 2.67 (t, 2H, J=7.6 Hz), 2.94 (t, 2H, J=7.6 Hz), 6.80 (m, 2H), 7.18 (dd, 1H, J=14.8 Hz and 8.0 Hz). The title A compound, (2,4-difluorophenyl)piperazin-1-yl-propanone hydrochloride is obtained analogously to the title B compound of Example 4 as a white solid: m.p=221° C. LC/MS (M+1=255.1). 1H NMR (DMSO-d6, 400 MHz) δ 2.66 (t, 2H, J=7.6 Hz), 2.81 (t, 2H, J=7.6 Hz), 3.01 (m, 2H), 3.05 (m, 2H), 3.69 (m, 4H), 7.02 (dt, 1H, J=8.4 Hz and 2.4 Hz), 7.18 (dt, 1H, J=10.0 Hz and 2 8 Hz), 7.29 (dd, 1H, J=15.6 Hz and 8.8 Hz), 9.65 (br s, NH). Anal. calculated for (C13H16F2N2O HCl+0.2 H2O): C, 53.05; H, 5.96; Cl, 12.04; F, 12.91; N, 9.52; O, 6.52. Found C, 53.01; H, 5.96; N, 9.74.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1a285130a6044c159dc8f1fae5a5fc8e
Source dataset
uspto-grants-2010_05
Patent number
US07723343B2

Reaction notes

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