[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][Li]>O1CCCC1>[C:1]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)(=[O:13])[CH3:14]Quinaldic acid (2.76 grams, 0.017 mole) was dissolved in 100 ml of dried tetrahydrofuran. Then 25 ml of 1.6 M (0.04 mole) of methyl lithium was added using a syringe. Reaction appeared immediate. The solution was stirred and heated under reflux for two hours and then poured into 600 ml of ice water. The ketone (2-acetylquinoline) was extracted with four 25 ml portions of ethyl ether which, after drying, was removed by rotary evaporation to yield ca. 1.0 g (ca. 40%) of 2-acetylquinoline.
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