Hydrochloric Acid → HCID 10647202, compound

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][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:7]([C:21]([O:23]CC)=[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.[OH-].[Na+].Cl>C(O)C>[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][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:7]([C:21]([OH:23])=[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

Participants

Procedure

A mixture of ethyl 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylate (3.0 g), 2N sodium hydroxide (15.6 ml) and ethanol (50 ml) was stirred under reflux for 8 hours. The reaction mixture was ice-cooled, adjusted to pH 5 with 2N hydrochloric acid and concentrated under reduced pressure. The residue was dissolved in ethanol, the insoluble materials were filtered off, and the filtrate was concentrated. The residual oil was subjected to column chromatography on silica gel. The fractions eluted with chloroform/methanol (4/1, v/v) gave 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid (1.3 g, 46%) which was then recrystallized from dichloromethane-ethanol. Colorless prisms. mp. 270°-271° C. (decomposition).