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 24552ノート

反応式

HRID 24552 の反応式
C([O:3][C:4]([C:6]1[NH:7][C:8]([CH:19]=O)=[C:9]([CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])[C:10]=1[CH3:11])=[O:5])C.[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([C:30]2[CH:38]=[C:37]3[C:33]([CH2:34][C:35](=[O:39])[NH:36]3)=[CH:32][CH:31]=2)[CH:27]=[CH:28][CH:29]=1)[CH3:22]>N1CCCCC1.C(O)C>[C:14]([CH2:13][CH2:12][C:9]1[C:10]([CH3:11])=[C:6]([C:4]([OH:3])=[O:5])[NH:7][C:8]=1[CH:19]=[C:34]1[C:33]2[C:37](=[CH:38][C:30]([C:26]3[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH2:21][CH3:22])[CH:25]=3)=[CH:31][CH:32]=2)[NH:36][C:35]1=[O:39])([OH:16])=[O:15]

参加物

5

反応物 2

HCID 106346366-(3-Ethoxyphenyl)indolin-2-oneHCID 110223335-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

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 80.4%

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-methyl-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-db20cfe9999f494d9de07936ff194186
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

反応ノート

読み込み中…