Hydrochloric Acid → HCID 10647202, compound

HRID 1584158Notes

Reaction equation

HRID 1584158 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:30][N:31]2[CH:35]=[N:34][CH:33]=[N:32]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)=[CH:13][C:12]([O:26][CH3:27])=[C:11]([O:28][CH3:29])[CH:10]=2)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH3:27][O:26][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:28][CH3:29])[N:8]=[C:7]([CH2:30][N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)[C:6]([C:4]([OH:5])=[O:3])=[C:15]2[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=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 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (3.0 g), 2 N sodium hydroxide (15.6 ml) and ethanol (50 ml) was stirred under refluxing conditions for 8 hours. The reaction mixture was cooled with ice and adjusted to pH 5 with 2 N hydrochloric acid, after which it was concentrated under reduced pressure. The residue was dissolved in ethanol, and the insoluble substances were filtered off. After the filtrate was concentrated, the residual oily substance was subjected to silica gel column chromatography and eluted with chloroform-methanol (4:1, v/v) to yield 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 to yield a colorless prismatic crystal having a melting point of 270 to 271° C. (decomposed).

Workup

  1. temperatureThe reaction mixture was cooled with ice
  2. concentrationafter which it was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol
  4. filtrationthe insoluble substances were filtered off
  5. concentrationAfter the filtrate was concentrated
  6. washeluted with chloroform-methanol (4:1

Sources & evidence

ORD record
ord-5d2040439e274a96a70959cc79449947
Source dataset
uspto-grants-1999_08
Patent number
US05932592

Reaction notes

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