HCID 15053184, compound → HCID 15053186, compound

HRID 1088821Notes

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH3:22])[CH2:19][CH2:18][C:17]2=[O:23].[CH3:24][Li]>O1CCCC1>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[S:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]([CH3:22])[CH2:19][CH2:18][C:17]2([OH:23])[CH3:24]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 8-(2-benzimidazolyl)thiomethyl-1-methyl-4-oxo-1,2,3,4-tetrahydroquinoline (300 mg) in tetrahydrofuran (10 ml) was added dropwise methyl lithium (1.5M solution in tetrahydrofuran) (1.33 ml) with stirring at -10° C. Then the mixture was stirred for 30 minutes at the same temperature. After distilling off the solvent, the residue was extracted with dichloromethane, washed with water, and dried, then the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate-dichloromethane (10:5:2)], and recrystallized from dichloromethane-diethyl ether to give 8-(2-benzimidazolyl)thiomethyl-4-hydroxy-1,4-dimethyl-1,2,3,4-tetrahydroquinoline (96 mg).

Workup

stirringThen the mixture was stirred for 30 minutes at the same temperature
distillationAfter distilling off the solvent
extractionthe residue was extracted with dichloromethane
washwashed with water
customdried
distillationthe solvent was distilled off
customThe resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate-dichloromethane (10:5:2)]
customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record: ord-33eeb942124044c9944c8eb72141a5b3
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04963566

Reaction notes

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