6-(3-Ethoxyphenyl)indolin-2-one → 4-(2-Carboxyethyl)-5-[6-(3-ethoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid

HRID 1860954ノート

反応式

HRID 1860954 の反応式
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:20]=O)=[C:9]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[C:10]=1[CH2:11]C)=[O:5])C.[CH2:22]([O:24][C:25]1[CH:26]=[C:27]([C:31]2[CH:39]=[C:38]3[C:34]([CH2:35][C:36](=[O:40])[NH:37]3)=[CH:33][CH:32]=2)[CH:28]=[CH:29][CH:30]=1)[CH3:23]>N1CCCCC1.C(O)C>[C:15]([CH2:14][CH2:13][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:20]=[C:35]1[C:34]2[C:38](=[CH:39][C:31]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH2:22][CH3:23])[CH:26]=3)=[CH:32][CH:33]=2)[NH:37][C:36]1=[O:40])([OH:17])=[O:16]

参加物

5

反応物 2

HCID 106346366-(3-Ethoxyphenyl)indolin-2-oneHCID 86758874HCID 86758874、化合物

生成物 1

HCID 536921164-(2-Carboxyethyl)-5-[6-(3-ethoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid収率 84.4%

試薬・触媒・溶媒 2

HCID 8082Piperidine触媒HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

A mixture of 5-formyl-4-(2-ethoxycarbonylethyl)-3-ethyl-1H-pyrrole-2-carboxylic acid ethyl ester (281 mg), 6-(3-ethoxyphenyl)-2-oxindole (304 mg), and piperidine (2 drops) in ethanol (5 mL) were held at 90° C. overnight. The precipitate that formed was filtered, washed with ethanol. The precipitate, an orange solid, was stirred with potassium hydroxide (4 pellets) in ethanol (3 mL) at 90° C. for 2.5 hours. The reaction mixture was cooled and concentrated. The residue was dissolved into water and acidified with 2N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 370 mg of 4-(2-Carboxyethyl)-5-[6-(3-ethoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid.

後処理

  1. customThe precipitate that formed
  2. filtrationwas filtered
  3. washwashed with ethanol
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved into water
  7. filtrationThe precipitate was filtered
  8. washwashed with water
  9. customdried in a vacuum oven overnight

出典と根拠

ORDレコード
ord-aa6707d517804284a28bfc2dccacc2c1
出典データセット
uspto-grants-2003_03
特許番号
US06531502B1

反応ノート

読み込み中…