4-Nitrophenol → 4-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 387969ノート

反応式

HRID 387969 の反応式
CN1CCCC1=O.C(N(C(C)C)CC)(C)C.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:19])=[O:18].[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38](Cl)=[C:33]2[CH:32]=1)=[O:30]>O>[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38]([O:26][C:23]3[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=3)=[C:33]2[CH:32]=1)=[O:30]

参加物

6

反応物 4

HCID 9804-NitrophenolHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 589308884-Chloro-furo[2,3-b]pyridine-2-carboxylic acid methyl ester

生成物 1

HCID 589314974-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester収率 4.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
140 °C

実験手順

After adding N-methylpyrrolidone (4.0 ml), diisopropylethylamine (1.3 ml) and para-nitrophenol (822 mg) to 4-chlorofuro[2,3-b]pyridine-2-carboxylic acid methyl ester (1.0 g), the mixture was heated and stirred at 140° C. for 5 hours. After cooling, water was added, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Tetrahydrofuran was used for recrystallization to obtain the title compound (70 mg).

後処理

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling
  3. extractionextraction
  4. washthe organic layer was washed with water and saturated saline in that order
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customTetrahydrofuran was used for recrystallization

出典と根拠

ORDレコード
ord-e932449599b64eeea7beccf39108804f
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

反応ノート

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