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

HRID 1956760노트

반응식

HRID 1956760 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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):

후처리

  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

출처 및 근거

ORD 기록
ord-f0247a1b54bb47bf9a99d43b443b7310
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05780634

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