Water → HCID 11797413, compound

HRID 1584146Notes

Reaction equation

C([O:3][C:4](=O)[CH2:5][C:6]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=2)[C:13]2[C:8](=[CH:9][C:10]([O:33][CH3:34])=[C:11]([O:31][CH3:32])[CH:12]=2)[N:7]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH2:19]([O:18][C:16]([C:15]1[C:6]([CH2:5][CH2:4][OH:3])=[N:7][C:8]2[C:13]([C:14]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)=[CH:12][C:11]([O:31][CH3:32])=[C:10]([O:33][CH3:34])[CH:9]=2)=[O:17])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl ester (5.8 g) in tetrahydrofuran (100 ml) was added drop by drop at 0° C. to a suspension of lithium aluminum hydride (0.455 g) in tetrahydrofuran (50 ml). After the reaction mixture was stirred at 0° C. for 1 hour, water (2.5 ml) was added drop by drop, followed by stirring for 30 more minutes. After the insoluble solid was filtered off, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (1:1, v/v) to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-quinoline-3-carboxylic acid ethyl ester (1.75 g, 33%), which was then recrystallized from ethyl acetate-hexane to yield a colorless prismatic crystal having a melting point of 150 to 151° C.

Workup

stirringby stirring for 30 more minutes
filtrationAfter the insoluble solid was filtered off
concentrationthe filtrate was concentrated under reduced pressure
washeluted with chloroform-ethyl acetate (1:1

Sources & evidence

ORD record: ord-489e7ed7bfb8404b88c884c6e387d33a
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05932592

Reaction notes

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