Hydrochloric Acid → HCID 10647202, compound

HRID 1458935Notes

Reaction equation

HRID 1458935 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 153980TAK-603

Product 1

HCID 10647202HCID 10647202, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. temperatureunder reflux for 8 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethanol
  5. filtrationthe insoluble materials were filtered off
  6. concentrationthe filtrate was concentrated
  7. washThe fractions eluted with chloroform/methanol (4/1

Sources & evidence

ORD record
ord-93e551f9f56a472990b4b47d843c5931
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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