ChemicalBook CAS DataBase List 3-(1-Naphthoyl)indole

3-(1-Naphthoyl)indole synthesis

5synthesis methods

Product Name:3-(1-Naphthoyl)indole
CAS Number:109555-87-5
Molecular formula:C19H13NO
Molecular Weight:271.31

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

120-72-9 Synthesis

120-72-9
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879-18-5 Synthesis

879-18-5
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109555-87-5
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Yield:109555-87-5 93%

Reaction Conditions:

with diethylaluminium chloride in toluene at 0 - 20; for 24 h;Friedel-Crafts Acylation;

Steps:

2.1 Synthesis of synthetic cannabinoids

General procedure: JWH-073 and JWH-018 were synthesized according to previous reports (Blaazer et al., 2011) in high yield (Fig.1). The intermediate (1H-indol-3-yl) (naphthalene-1-yl)methanone (2) was prepared by Friedel-Crafts acylation of indole (1) with 1-naphthoyl chloride in the presence of diethylaluminium chloride in toluene. In order to obtain (2) in high yield, the optimal reaction conditions were performed with different molar ratios of 1-naphthoyl chloride, indole and amount of diethylaluminum chloride and purification was achieved via column chromatography or recrystallization. Each of the final compounds was purified using hexane and ethyl acetate (95:5, v/v) by column chromatography to give JWH-073 and JWH-018 as an oily yellow gum. For the intermediate, a molar ratio of 1.2-1.4 times of indole to 1-naphthoyl chloride and diethylaluminium chloride achieved a yield of 85-93%. Subsequent N-alkylation with 1-bromobutane and 1-bromopentane using potassium hydroxide and dimethylformamide in acetone provided JWH-073 and JWH-018.

References:

Cooper, Ziva D.;Poklis, Justin L.;Liu, Fei [Neuropharmacology,2018,vol. 134,p. 92 - 100]

120-72-9 Synthesis

120-72-9
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