Water → HCID 11797413, compound

HRID 862631Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[C:8]([CH2:15][C:16](OCC)=[O:17])[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:6]2[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[OH:17][CH2:16][CH2:15][C:8]1[C:7]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:6]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH3:35])[CH:27]=2)[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetate (5.8 g) in tetrahydrofuran (100 ml) was added dropwise to a suspension of lithium aluminium hydride (0.455 g) in tetrahydrofuran (50 ml) at 0° C. After stirring the reaction mixture at 0° C. for 1 hour, water (2.5 ml) was added dropwise, and the mixture was stirred for additional 30 minutes. The insoluble solid was filtered off, 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 2-(2-hydroxyethyl)-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (1.75 g, 33%) which was then recrystallized from ethyl acetate-hexane. Colorless prisms. mp. 150°-151° C.

Workup

stirringthe mixture was stirred for additional 30 minutes
filtrationThe insoluble solid was filtered off
concentrationthe filtrate was concentrated under reduced pressure
washThe fractions eluted with chloroform/ethyl acetate (1/1

Sources & evidence

ORD record: ord-77211ab0f4c94730897f849ec3464976
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719157

Reaction notes

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