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

HRID 458167Notes

Reaction equation

HRID 458167 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 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

2,3,4-Trifluoroaniline (0.83 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 for 2 hours. After filtering off Pd—C, the obtained filtrate was concentrated under reduced pressure. Thus the title compound (1.26 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-9d3d454e6c1348efada242a0563070bb
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

Loading…