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

HRID 1860888노트

반응식

HRID 1860888 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

실험 절차

A mixture of 5-carboxy-2-oxindole (88.5 mg), indole-2-carbaldehyde (87 mg) (prepared according to Synthetic Communications, 1993, 23, 3109) and piperidine (1 drop) in ethanol (3 mL) was held 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 solid was collected by vacuum filtration, washed with cold ethanol and dried in vacuum oven 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. filtrationThe solid was filtered
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washwashed with cold ethanol
  4. customdried in vacuum oven

출처 및 근거

ORD 기록
ord-ad8c008e539f487b9db8a5f30890f3eb
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531502B1

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