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

HRID 1956760ノート

反応式

HRID 1956760 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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):

後処理

  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

出典と根拠

ORDレコード
ord-f0247a1b54bb47bf9a99d43b443b7310
出典データセット
uspto-grants-1998_07
特許番号
US05780634

反応ノート

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