Water → HCID 11797413, compound

HRID 266125Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[C:13]([CH2:25][C:26](OCC)=[O:27])[C:12]=2[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[C:13]([CH2:25][CH2:26][OH:27])[C:12]=2[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3-ethoxycarbonylquinoline-2-acetate (5.8 g) in tetrahydrofuran (100 ml) was added dropwise to a suspension of lithium aluminum hydride (0.455 g) in tetrahydrofuran (50 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour, and then water (2.5 ml) was added dropwise, and the mixture was stirred for 30 minutes. The insoluble solids were separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (1:1, v/v) gave ethyl 4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinoline-3-carboxylate (1.75 g, 33%). This was recrystallized from ethyl acetate-hexane. Colorless prisms, mp. 150°-151° C.

Workup

stirringthe mixture was stirred for 30 minutes
customThe insoluble solids were separated by filtration
concentrationthe filtrate was concentrated under reduced pressure
washThe fractions eluted with chloroform-ethyl acetate (1:1

Sources & evidence

ORD record: ord-5e617c32ca314b9bb54adaabb288c9ab
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05650410

Reaction notes

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