Dimethylformamide → 1-benzyl-2,3-dihydroindole-5-carbaldehyde

HRID 1108479노트

반응식

HRID 1108479 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)[CH:19]=[O:20].P(Cl)(Cl)(Cl)=O.[OH-].[Na+]>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:19]=[O:20])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 108050961-Benzylindoline

생성물 1

HCID 9275671-benzyl-2,3-dihydroindole-5-carbaldehyde수율 97%

반응 조건

온도
35 °C

실험 절차

Into a 1,000 mλ reaction flask equipped with a thermometer, a stirrer, a condenser and a dropping funnel, 209 g (1.0 mol) of 1-benzylindoline and 365.5 g (5.0 mols) of N,N-dimethylformamide (DMF) were charged, and the temperature was raised to a liquid temperature of from 30 to 40° C. Then, while stirring at the same temperature, 161.0 g (1.05 mols) of phosphorus oxychloride was dropwise added thereto over a period of about two hours from the dropping funnel. After completion of the dropwise addition, stirring was continued for three hours at from 80 to 100° C. After completion of the reaction, the reaction solution was cooled to room temperature and put into 1 kg of ice water. At a temperature of from 30 to 40° C., a 24% sodium hydroxide aqueous solution was dropwise added thereto to bring the liquid alkaline, whereby the precipitated solid was collected by filtration, washed with water and dried to obtain 230.2 g (yield: 97%) of 1-benzyl-5-formylindoline as a slightly yellow powder.

후처리

  1. customInto a 1,000 mλ reaction flask
  2. additionwere charged
  3. additionwas dropwise added
  4. additionAfter completion of the dropwise addition
  5. waitwas continued for three hours at from 80 to 100° C
  6. customAfter completion of the reaction
  7. temperaturethe reaction solution was cooled to room temperature
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. customdried

출처 및 근거

ORD 기록
ord-8cdebfb63b45487fb656b36d14763335
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066744

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