Water → 2-(2-Methoxycarbonyl-phenyl)-6-methyl-4-quinolinecarboxylic acid

HRID 1956760Notes

Reaction equation

HRID 1956760 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:20]=[C:19]([C:21]([O:23]C)=[O:22])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:25])[CH:17]=2)[N:12]=1)=[O:4].[OH-].[Na+].O>CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH3:25])[CH:17]=2)[N:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 229156284-Quinolinecarboxylic acid,2-[2-(methoxycarbonyl)phenyl]-6-methyl-,methyl ester

Product 1

HCID 218016092-(2-Methoxycarbonyl-phenyl)-6-methyl-4-quinolinecarboxylic acidYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 2 ml of methanol were dissolved 377 mg (1.23 mmol) of methyl 2-(2-methoxycarbonylphenyl)-6-methyl-4-quinolinecarboxylate obtained in Example 3 and 49 mg (1.2 mmol) of sodium hydroxide. 3 ml of water were added thereto and the resulting mixture was stirred for 24 hours. After concentrated under reduced pressure, water was added to the residue, the aqueous layer was acidified and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate followed by distillation under reduced pressure. The resulting residue was purified by flash silica gel chromatography using a mixed solvent of chloroform and methanol (70/1) to obtain 267 mg of 2-(2-methoxycarbonyl-phenyl)-6-methyl-4-quinolinecarboxylic acid. NMR (270 MHz, CD3OD):

Workup

  1. concentrationAfter concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. distillationfollowed by distillation under reduced pressure
  6. customThe resulting residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-f0247a1b54bb47bf9a99d43b443b7310
Source dataset
uspto-grants-1998_07
Patent number
US05780634

Reaction notes

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