Indole → 3-Naphthoylindole

HRID 55921

반응식

HRID 55921 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C[Mg]Br.[C:13]1([C:23](Cl)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>CCOCC>[C:13]1([C:23]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 798IndoleHCID 25517Ammonium ChlorideHCID 701461-Naphthalenecarbonyl chlorideHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 103558253-Naphthoylindole수율 91%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

To a cooled solution of indole (5.85 g, 50 mmol) in ether (50 ml) under nitrogen was added slowly a solution of methylmagnesium bromide (3M) in ether (17.5 ml). After addition, the reaction mixture was warmed up to room temperature and stirred for 2 h at room temperature. Then the mixture was cooled down again to 0° C., and to it was added slowly with stirring a solution of 1-naphthoylchloride (9.5 g, 50 mmol) in ether (50 ml). The resulting mixture was warmed up to room temperature and stirred for 2 h at room temperature followed by slow addition of saturated ammonium chloride solution (375 ml). The mixture was then stirred overnight at room temperature. A white solid was formed, filtered, washed by ether and dried under high vacuum to give 3-(1-naphthoyl)-1H-Indole 1 (12.3 g, 91%).

후처리

  1. additionAfter addition
  2. temperatureThen the mixture was cooled down again to 0° C.
  3. additionto it was added slowly
  4. temperatureThe resulting mixture was warmed up to room temperature
  5. stirringstirred for 2 h at room temperature
  6. stirringThe mixture was then stirred overnight at room temperature
  7. customA white solid was formed
  8. filtrationfiltered
  9. washwashed by ether
  10. customdried under high vacuum

출처 및 근거

ORD 기록
ord-8a303a3c232549e4839a627077ca7aa6
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434687B2

연결된 노트

불러오는 중…