Toluene → 8-Ethynylquinoline

Temperature

120 °C

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%).

1. customequipped with a reflux condenser
2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
3. dry with materialdried over magnesium sulfate
4. distillationthe solvent was distilled off under reduced pressure by an evaporator
5. additionHexane (250 ml) was added to the residue
6. temperaturethe mixture was heated to 70° C
7. filtrationAfter filtering out the insolubles
8. customthe desired compound precipitated
9. temperatureby cooling it to −78° C.
10. filtrationwas filtered
11. washwashed with cold hexane (−78° C., 100 ml)
12. customdried under reduced pressure

ORD record

ord-ed1c3f9ebc774bb194c4b05a38f39d01

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08137821B2