Hydrochloric Acid → HCID 68496119, compound

Participants

Reaction Steps

5-(5-Nitropyridin-2-yloxy)-1H-indole (3.00 g, 11.8 mmol) was dissolved in 1,4-dioxane (30 mL). To the solution were added boran-trimethylamine complex (3.43 g, 47.0 mmol) and hydrochloric acid (1.96 mL, 23.5 mmol) and the resulting solution was refluxed for 1 hour. After cooling for 30 minutes, 6 M hydrochloric acid (9.40 mL, 56.4 mmol) was added to the solution, and the mixture was refluxed again. Thirty minutes later, the reaction mixture was cooled with ice and the pH of the solution was adjusted to 8 by dropwise addition of concentrated aqueous sodium hydroxide. Water (150 mL) was added to the solution, and the mixture was extracted with ethyl acetate (150 mL). After the organic layer was washed with brine, then dried over anhydrous sodium sulfate, the solvent was evaporated to yield 2.82 g of the title compound as reddish orange oil.

Provenance & Evidence