Selenium Dioxide → Methyl 2-oxo-2-(quinolin-6-yl)acetate

HRID 1661807Notes

Reaction equation

HRID 1661807 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Se](=O)=[O:17]>O1CCOCC1>[CH3:15][O:14][C:12](=[O:13])[C:11](=[O:17])[C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 1514202Methyl 6-quinolineacetate

Product 1

HCID 57654511Methyl 2-oxo-2-(quinolin-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the solution of methyl 6-quinolineacetate (1.2 g, 6 mmmol) in dioxane (30 mL) was added Selenium dioxide (1.65 g, 15 mmol). The mixture was heated to reflux for 3 days, cooled to room temperature, filtered through Celite and concentrated. The residue was purified by chromatography (methylene chloride to 5% ethyl acetate in chloride) to a white solid (0.75 g, 58%). 1H-NMR (CDCl3): δ 9.07-9.06 (1H, q, J=1.7, 2.5 Hz), 8.62-8.61 (1H, d,J=1.7 Hz), 8.32-8.31 (2H, m), 8.22-8.20 (1H, d, J=8.8 Hz), 7.54-7.51 (1H, q, J=8.8Hz), 4.05 (3H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 days
  3. filtrationfiltered through Celite
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (methylene chloride to 5% ethyl acetate in chloride) to a white solid (0.75 g, 58%)

Sources & evidence

ORD record
ord-84ad915b0ec94039bfacd22432432619
Source dataset
uspto-grants-2011_10
Patent number
US08030305B2

Reaction notes

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