Methanol → Methyl 8-hydroxy-2-quinolinepropanoate

HRID 655889Notes

Reaction equation

HRID 655889 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])[CH:15]=[CH:14]2)C1C=CC=CC=1.S(Cl)(Cl)=O.[CH3:28]O>[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:28])=[O:22])[CH:15]=[CH:14]2

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 59134936HCID 59134936, compound

Product 1

HCID 59134930Methyl 8-hydroxy-2-quinolinepropanoateYield 70%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (E)-3-[8-(benzyloxy)-2-quinolinyl]-2-propenoic acid (8d) (0.3 g, 0.98 mmol) in methanol (15 ml), 5% palladium on activated carbon (0.03 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) and the column was washed with methanol (10 ml). To the obtained filtrate, at room temperature, thionyl chloride (0.2 g, 1.7 mmol) was added with vigorous stirring. The reaction mixture was stirred overnight and then evaporated in vacuo. To the residue, a solution of 5% NaHCO3 (20 ml) was added and the mixture was extracted with ethyl acetate (50 ml). The extract was dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel with ether-petrol ether (1:2) as eluent to afford the title compound (0.158 g, 70%) as an oil. 1H NMR (CDCl3, HMDSO), δ: 2.89 (2H, t, J=7.0 Hz); 3.32 (2H, t, J=7.0 Hz); 3.65 (3H, s); 7.09 (1H, dd, J=2.0 and J=6.0 Hz); 7.16-7.49 (3H, m); 8.01 (1H, d, J=8.6 Hz).

Workup

  1. filtrationThe reaction mixture was filtered through a short column of silica gel (ca. 2 g)
  2. washthe column was washed with methanol (10 ml)
  3. stirringThe reaction mixture was stirred overnight
  4. customevaporated in vacuo
  5. additionTo the residue, a solution of 5% NaHCO3 (20 ml) was added
  6. extractionthe mixture was extracted with ethyl acetate (50 ml)
  7. dry with materialThe extract was dried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica gel with ether-petrol ether (1:2) as eluent

Sources & evidence

ORD record
ord-9c133e5c6a7f45709c42c7967a507924
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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