Methanol → HCID 22097630, compound

HRID 1458926Notes

Reaction equation

HRID 1458926 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-1af75558d332415fa3956087430d2fa3
Source dataset
uspto-grants-1998_12
Patent number
US05852039

Reaction notes

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