Indole → 3-Naphthoylindole

HRID 1399476

Reaction equation

HRID 1399476 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 103558253-NaphthoylindoleYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b69bec5ad1684caaadfe16aec74c23c4
Source dataset
uspto-grants-2014_12
Patent number
US08906633B2

Linked notes

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