Methanol → Methyl 3-(2-quinolinyl)propanoate

HRID 655879Notes

Reaction equation

HRID 655879 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14].[CH3:16]O>[Pd]>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 887MethanolHCID 7129193-(2-Quinolinyl)-2-propenoic acid

Product 1

HCID 59134937Methyl 3-(2-quinolinyl)propanoateYield 43%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of methyl (E)-3-(2-quinolinyl)-2-propenoate (2) (0.26 g 1.22 mmol) in methanol (5 ml), 5% palladium on activated carbon (0.05 g) was added and the resulting suspension was hydrogenated by vigorous stirring for 2 hours at room temperature. The reaction mixture was filtered through a short column of silica gel (ca. 2 g), the column was washed with methanol (3 ml), and the filtrate was evaporated in vacuo. The residue (0.270 g) was chromatographed on silica gel (10 g) with chloroform-ethyl acetate (9:1) as eluent to afford the title compound (0.111 g, 43%) as an oil. 1H NMR (CDCl3, HMDSO), δ: 2.93 (2H, t, J=7.2 Hz); 3.29 (2H, t, J=7.2 Hz); 3.67 (3H, s); 7.29-7.85 (4H, m); 7.89-8.11 (2H, m).

Workup

  1. filtrationThe reaction mixture was filtered through a short column of silica gel (ca. 2 g)
  2. washthe column was washed with methanol (3 ml)
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue (0.270 g) was chromatographed on silica gel (10 g) with chloroform-ethyl acetate (9:1) as eluent

Sources & evidence

ORD record
ord-dc521c9b0b5d4a419c58f2cf95f0c494
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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