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

HRID 985654Notes

Reaction equation

HRID 985654 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-])=O.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[C:14]([CH3:16])=O.Cl>C(O)C.[Pd]>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][CH:14]([CH3:16])[C:13]([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 12041Ethyl pyruvateHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 22015871Ethyl 2-(2,3,4-trifluoroanilino)propionateYield 97.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

2,3,4-Trifluoronitrobenzene (1.01 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 (1.38 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-619afafe6c574d30bb7e020c65e8bac2
Source dataset
uspto-grants-2005_03
Patent number
US06872823B1

Reaction notes

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