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

HRID 8435

Reaction equation

HRID 8435 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-70f6d86b6a29466c9e871d6a54e57035
Source dataset
uspto-grants-2006_08
Patent number
US07087778B2

Linked notes

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