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 24552노트

반응식

HRID 24552 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.[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 536921164-(2-Carboxyethyl)-5-[6-(3-ethoxyphenyl)-2-oxo-1,2-dihydroindol-3-ylidenemethyl]-3-methyl-1H-pyrrole-2-carboxylic acid수율 80.4%

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-db20cfe9999f494d9de07936ff194186
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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