Hydrochloric Acid → Ethyl 2-(2,3,4-trifluoroanilino)propionate

HRID 458168Notes

Reaction equation

HRID 458168 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[C:12]([CH3:14])=O.Cl>C(O)C.[Pd]>[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[NH:4][CH:12]([CH3:14])[C:11]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12041Ethyl pyruvateHCID 774682,3,4-Trifluoroaniline

Product 1

HCID 22015871Ethyl 2-(2,3,4-trifluoroanilino)propionateYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

2,3,4-Trifluoroaniline (0.83 g) and ethyl pyruvate (1.15 g) were dissolved in ethanol (8 ml). After adding 5% Pd—C (0.11 g) and conc. hydrochloric acid (0.03 g), the mixture was stirred at 40° C. under a hydrogen gas pressure of 2.94 MPa for 3 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the title compound (1.32 g) was obtained as slightly yellow oily substance. Various spectral data of this product was identical with those obtained in Example 7.

Workup

  1. filtrationAfter filtering off Pd—C
  2. concentrationthe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d78b936f696b49e683a4f33d55dca1d8
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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