Diethyl Oxalate → Ethyl 2-oxo-2-(quinolin-6-yl)acetate

HRID 469189Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[Li+].[Cl-].[CH2:14]([O:16][C:17](=[O:23])[C:18](OCC)=[O:19])[CH3:15]>C1COCC1>[O:19]=[C:18]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[C:17]([O:16][CH2:14][CH3:15])=[O:23]

Participants

Conditions

Temperature: -20 °C

Procedure

Under inert atmosphere 255 g 6-iodoquinoline (1 mol) is dissolved in THF and cooled to −20° C. and 808 g IpMgCl.LiCl (1.1 moles) is added. This cold solution is added to a solution of 438 g diethyloxalate (3 moles) in 1800 mL THF at low temperature (−78° C.). The reaction mixture is heated to 0° C. and is quenched with a saturated ammonium acetate solution (0.8 L/mole). Ethyl oxo(quinolin-6-yl)acetate is extracted with ethyl acetate (1 L) from this mixture. After chromatography (silica, heptanes/ethyl acetate) ethyl oxo(quinolin-6-yl)acetate was obtained in 70% yield.

Workup

temperatureThe reaction mixture is heated to 0° C.
customis quenched with a saturated ammonium acetate solution (0.8 L/mole)
extractionEthyl oxo(quinolin-6-yl)acetate is extracted with ethyl acetate (1 L) from this mixture

Sources & evidence

ORD record: ord-0e39bf9c241549ec921635e5eabbbba5
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629144B2

Reaction notes

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