Ammonia → 1-(8-Quinolyl)-2-methylindene

HRID 47836

Reaction equation

[Li]CCCC.[CH3:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=O.Br[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.Cl.N>C1COCC1>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][C:21]=2[CH:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:7]2[CH3:6])[CH:26]=[CH:27][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6.70 ml of n-BuLi (16.8 mmol) were added dropwise at 100° C. to 3.50 g of o-bromoquinoline (16.8 mmol) dissolved in 50 ml of THF, and the mixture was subsequently stirred at 80° C. for 15 minutes. A solution of 50 ml of THF and 2.45 g of 2-methyl-1-indanone (16.8 mmol) was then added to the lithiated bromoquinoline over the course of 10 minutes. The mixture was allowed to cool to room temperature, and the solution was then refluxed for three hours, cooled to room temperature, acidified to pH 1 using ice and hydrochloric acid and subsequently refluxed for three hours. The reaction mixture was adjusted to pH 9 using ammonia solution, and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried, and the solvent was removed. The crude product was purified by distillation under reduced pressure at 150-160° C./10−2 mbar, giving 1.5 g of 1-(8-quinolyl)-2-methylindene (45%) as a yellow, viscous resin.

Workup

temperatureto cool to room temperature
temperaturethe solution was then refluxed for three hours
temperaturecooled to room temperature
temperaturesubsequently refluxed for three hours
extractionthe aqueous phase was extracted with diethyl ether
customThe combined organic phases were dried
customthe solvent was removed
distillationThe crude product was purified by distillation under reduced pressure at 150-160° C./10−2 mbar

Sources & evidence

ORD record: ord-7463d25ec540496fbca7fac791393efd
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699948B2

Linked notes

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