HCID 23346132, compound → HCID 23346097, compound

HRID 1856205Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]([C:21]([F:24])([F:23])[F:22])([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:15](=[O:20])[CH2:16][C:17](=O)[CH3:18])[CH2:10][CH2:9][CH2:8]2)[OH:4]>S(=O)(=O)(O)O>[F:26][C:2]([F:25])([F:1])[C:3]([C:5]1[CH:6]=[C:7]2[C:12]3[N:11]([CH2:10][CH2:9][CH2:8]2)[C:15](=[O:20])[CH:16]=[C:17]([CH3:18])[C:13]=3[CH:14]=1)([OH:4])[C:21]([F:24])([F:23])[F:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred mixture of 6.0 g (0.02 mole) of α,α-bis(trifluoromethyl)-1,2,3,4-tetrahydro-6-quinolinemethanol, 2.6 g (0.02 mole) of ethyl acetoacetate, and 100 ml of xylene is refluxed for 16 hours. The mixture is allowed to cool and is evaporated. The residue is triturated with a mixture of toluene, ethyl acetate, and hexane (60:10:30). The insoluble portion is filtered off, washed with water, and dried to give 1.6 g (23%) of α,α-bis(trifluoromethyl)-1-(1,3-dioxobutyl)-1,2,3,4-tetrahydro-6-quinolinemethanol. C. A solution of 10.5 g (0.027 mole) of α,α-bis(trifluoromethyl)-1-(1,3-dioxobutyl)-1,2,3,4-tetrahydro-6-quinolinemethanol in 30 ml of concentrated sulfuric acid is heated on a steam bath for 30-45 minutes, cooled to approximately 60° C., and poured into ice. When the ice is melted, the precipitate is filtered off, washed with water, and dried. The solid is recrystallized from 2-ethoxyethanol to give 7.2 g (74% ) of 2,3-dihydro-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-7-methyl-1H,5H-benzo[ij]quinolizin-5-one, m.p. 295°-296°.

Workup

additionpoured into ice
filtrationthe precipitate is filtered off
washwashed with water
customdried
customThe solid is recrystallized from 2-ethoxyethanol

Sources & evidence

ORD record: ord-1c8b20db1050493b8873643f94e6f9bd
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04218448

Reaction notes

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