Piperidine → 4-(2-carboxyethyl)-3-methyl-5-(6-methoxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid

HRID 24538

반응식

HRID 24538 반응식
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.[CH3:21][O:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][C:28](=[O:32])[NH:29]2)=[CH:25][CH:24]=1.N1CCCCC1.[OH-].[K+]>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:27]1[C:26]2[C:30](=[CH:31][C:23]([O:22][CH3:21])=[CH:24][CH:25]=2)[NH:29][C:28]1=[O:32])([OH:16])=[O:15]

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 14797Potassium HydroxideHCID 27937496-MethoxyoxindoleHCID 110223335-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

생성물 1

HCID 536903224-(2-carboxyethyl)-3-methyl-5-(6-methoxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid수율 99%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
95 °C

실험 절차

5-Formyl-4-(2-ethoxycarbonylethyl)-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (591 mg), 6-methoxy-2-oxindole (333 mg) and piperidine (0.1 mL) in ethanol (4 mL) were stirred at 90° C for 2 hours. Potassium hydroxide (537 mg) was added to the mixture and it was then stirred at 95° C. for and additional hour. The reaction mixture was cooled and concentrated, dissolved in water, and acidified with 2 N hydrochloric acid to pH 2. The precipitate was filtered, washed with water, and dried in a vacuum oven overnight to give 730 mg (99%) of 4-(2-carboxyethyl)-3-methyl-5-(6-methoxy-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrole-2-carboxylic acid.

후처리

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. dissolutiondissolved in water
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-af289579989748c1aca026cdf56f41e5
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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