Nitrogen → 2-Methyl-3-trichloroacetyl-7-methoxyindole

Beteiligte Stoffe

Reaktionsschritte

To a 2 L round-bottomed flask equipped with a magnetic stirrer and a N2 bubbler were added 2-methyl-7-methoxyindole (12 g, 74 mmol), acetonitrile (125 mL) and collidine (15 mL, 113 mmol). The mixture was stirred to give a solution and was cooled with an ice water bath. Trichloroacetyl chloride (14 mL, 112 mmol) was added. The cooling bath was removed and the reaction mixture stirred at RT for 3 h. 1N HCl (500 mL) was then added over 10 minutes. The resulting slurry was stirred at RT for 30 minutes and filtered. The cake was washed with DI water (3×50 mL) and suction dried for 17 h to give 2-methyl-3-trichloroacetyl-7-methoxyindole (22.8 g, 96% yield). 1H NMR (CDCl3) δ2.79 (s, 3H), 3.96 (s, 3H), 6.71 (d, J=7.9 Hz, 1H), 7.19 (dd, J=7.9, 8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 8.92 (s, 1H).

Herkunft & Nachweise