Indole → 3-Naphthoylindole

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%).

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

ORD-Eintrag

ord-b69bec5ad1684caaadfe16aec74c23c4

Quelldatensatz

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08906633B2