Methanol → HCID 22097630, compound

HRID 862636Notes

Reaction equation

HRID 862636 reaction equation
[CH2:1]([C:3]1[C:12]([C:13]([O:15]C)=[O:14])=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[C:10]2[C:5](=[CH:6][C:7]([O:29][CH3:30])=[C:8]([O:27][CH3:28])[CH:9]=2)[N:4]=1)[CH3:2].[OH-].[Na+].CO>O>[CH3:28][O:27][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[O:29][CH3:30])[N:4]=[C:3]([CH2:1][CH3:2])[C:12]([C:13]([OH:15])=[O:14])=[C:11]2[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 9931431HCID 9931431, compound

Product 1

HCID 22097630HCID 22097630, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-ethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (0.5 g), 4N sodium hydroxide (20 ml) and methanol was stirred for 14 hours under reflux, poured into water, made acidic and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-ethylquinoline-3-carboxylic acid (0.343 g, 71%) which was then recrystallized from acetone-methanol. mp. 264°-267° C.

Workup

  1. temperatureunder reflux
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7d5528bf5f18474a921c97445b9932fd
Source dataset
uspto-grants-1998_02
Patent number
US05719157

Reaction notes

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