Indole → 3-Naphthoylindole

HRID 55921

反応式

HRID 55921 の反応式
[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

参加物

6

反応物 4

HCID 798IndoleHCID 25517Ammonium ChlorideHCID 701461-Naphthalenecarbonyl chlorideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 103558253-Naphthoylindole収率 91%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒3 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8a303a3c232549e4839a627077ca7aa6
出典データセット
uspto-grants-2016_09
特許番号
US09434687B2

関連ノート

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