methyl (E)-3-(3-quinolinyl)-2-propenoate → HCID 11053048, compound

HRID 653960Notes

Reaction equation

HRID 653960 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2

Participants

4

Reactant 1

HCID 1491214methyl (E)-3-(3-quinolinyl)-2-propenoate

Product 1

HCID 11053048HCID 11053048, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (E)-3-(3-quinolinyl)-2-propenoic acid methyl ester (3.6 g, 16.9 mmol) and 5% Pd/C (0.4 g) in EtOAc (300 mL) was hydrogenated at atmospheric pressure. Upon sessation of hydrogen uptake, the catalyst was separated by filtration through a pad of Celite and the filtrate was evacuated to dryness to give the crude product (3.48 g) which was purified via flash chromatography eluting with a mixture of CH2Cl2 and ether (1:1) to give 3-quinolinepropanoic acid methyl ester (2.77 g, 12.9 mmol) in 76% yield as a glass.

Workup

  1. customUpon sessation of hydrogen uptake, the catalyst was separated by filtration through a pad of Celite
  2. customthe filtrate was evacuated to dryness
  3. customto give the crude product (3.48 g) which
  4. customwas purified via flash chromatography
  5. washeluting with a mixture of CH2Cl2 and ether (1:1)

Sources & evidence

ORD record
ord-b4f9707a6e1142d6bcfb54e80253646b
Source dataset
uspto-grants-1992_07
Patent number
US05128448

Reaction notes

Loading…