Indole-2-carboxaldehyde → 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid

HRID 1840491노트

반응식

HRID 1840491 반응식
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([OH:3])=[O:2].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH:23]=O>N1CCCCC1.C(O)C>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[CH:23]=[C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[NH:9][C:8]1=[O:13]

참가 물질

5

반응물 2

HCID 96389Indole-2-carboxaldehydeHCID 27733182-Oxindole-5-carboxylic acid

생성물 1

HCID 540903703-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid수율 40%

시약·촉매·용매 2

HCID 8082Piperidine촉매HCID 702Ethanol용매

반응 조건

온도
95 °C

실험 절차

A mixture of 5-carboxy-2-oxindole (88.5 mg) (prepared as described in Compound IN-05), indole-2-carbaldehyde (87 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) and piperidine (1 drop) in ethanol (3 mL) was heated in a sealed tube at 95° C. for 4 hours. The mixture was cooled to room temperature. The solid was filtered and acidified with 2N hydrochloric acid. The resulting darker solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven for overnight to give 60 mg (40% yield) of 3-(1H-indol-2-ylmethylene)-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid as a mustard-colored solid.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe solid was filtered
  3. filtrationThe resulting darker solid was collected by vacuum filtration
  4. washwashed with cold ethanol
  5. customdried in vacuum oven for overnight

출처 및 근거

ORD 기록
ord-c97db97c0d9b49a784ee8ca5880e5230
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680335B2

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