Hydrochloric Acid → Methyl2-(2,3,4-trifluoroanilino)propionate

HRID 458165Notes

Reaction equation

HRID 458165 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][CH3:17])(=[O:15])[C:12]([CH3:14])=O.Cl>CO.[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][CH3:17])=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11748Methyl pyruvateHCID 774682,3,4-Trifluoroaniline

Product 1

HCID 22015876Methyl2-(2,3,4-trifluoroanilino)propionateYield 81.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

2,3,4-Trifluoroaniline (1.01 g) and methyl pyruvate (0.87 g) were dissolved in methanol (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 (converted from 30 kgf/cm2) for 2 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the title compound (1.31 g) was obtained as slightly yellowish crystals. Various spectral data of this product was identical with those obtained in Example 5.

Workup

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

Sources & evidence

ORD record
ord-1a56ed7d08a643a48e123d05d9d6f60d
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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