Sodium Hydroxide → 5-(1-Methyl-1H-indol-3-yl)tetrazole

Participants

Reaction Steps

3-Cyano(1-methyl-1H-indole) (J. Med. Chem. 199, 34, 147) (0.500 g, 3.21 mmol) was dissolved in dry DMF (4 ml) and treated with ammonium chloride (0.214 g, 4.01 mmol) and sodium azide (0.260 g, 4.01 mmol). The mixture was then heated to reflux with stirring. After 26 h, the reaction mixture was allowed to cool and was evaporated under reduced pressure to give a brown oil. Water (15 ml) was added to this residue whereupon it solidified. The mixture was made strongly basic with sodium hydroxide solution and then extracted with diethyl ether. The aqueous layer was then treated with activated charcoal and heated on a water bath for 10 minutes. The mixture was then filtered and the filtrate acidified with 5M HCl to pH4. The resulting brown precipitate was then filtered off and dried in vacuo to give the title compound (0.125 g, 20%) as a pale brown solid.

Provenance & Evidence