Ethyl 3-quinolineacrylate → Ethyl 3-(1,2,3,4-tetrahydroquinolin-3-yl)propanoate

HRID 53218Notes

Reaction equation

HRID 53218 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:2]=1>C(OCC)(=O)C.C(O)C.[Pd]>[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2]1

Participants

4

Reactant 1

HCID 53657281Ethyl 3-quinolineacrylate

Product 1

HCID 12415773Ethyl 3-(1,2,3,4-tetrahydroquinolin-3-yl)propanoateYield 26.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of ethyl β-(3-quinolyl)acrylate (100 mg, 0.44 mmol) and 50 mg of 10% Pd/C in ethyl acetate/ethanol (3 ml/1 ml) was hydrogenated under hydrogen (55 psi) for 1 h. The mixture was filtered through celite, the residue was washed with methylene chloride, and the combined organic layer was concentrated in vacuo. Upon chromatographic purification on 20 cm silica column (ethyl acetate/hexane, 1/8-1/2), 49 mg (50%) of ethyl 3-(3-quinolyl)propionate (KUO-1953-136B) and 27 mg (26%) of ethyl 3-(1,2,3,4-tetrahydro-3-quinolyl)propionate was isolated.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe residue was washed with methylene chloride
  3. concentrationthe combined organic layer was concentrated in vacuo
  4. customUpon chromatographic purification on 20 cm silica column (ethyl acetate/hexane, 1/8-1/2), 49 mg (50%) of ethyl 3-(3-quinolyl)propionate (KUO-1953-136B)

Sources & evidence

ORD record
ord-cbe7aeac66bf44a498ef90801ba2e9cb
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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