Toluene → 8-Ethynylquinoline

Participants

Reaction Conditions

Reaction Steps

8.5 g (40 mmol) of Dimethylhydroxymethyl-8-quinolylacetylene and 1. g (45 mmol) of sodium hydroxide (manufactured by KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 300 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with argon gas. 200 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 0.5 hours. Diethyl ether was added to the reaction mixture, the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure by an evaporator. Hexane (250 ml) was added to the residue and the mixture was heated to 70° C. After filtering out the insolubles, the desired compound precipitated by cooling it to −78° C. was filtered and washed with cold hexane (−78° C., 100 ml) and then dried under reduced pressure to give 4.9 g of the desired compound as a yellowish white solid (yield: 80%).

Provenance & Evidence