Hydrochloric Acid → HCID 178497028, compound

Participants

Reaction Steps

To a stirred solution of sodium nitrite (68.4 g, 991.3 mmol) in water (1425 mL) was added methyl 6-bromo-1H-indole-4-carboxylate (20.64 g, 81.25 mmol) at RT and the mixture stirred for 15 min at RT. To the mixture was added 6N HCl (159.6 mL) slowly dropwise over a period of 1 h and the reaction mixture was then stirred at room temperature for 48 h. The reaction mixture was extracted with 10% THF in ethyl acetate (5×500 mL). The combined organic layers were washed with water, brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to ⅓ volume and cooled in freezer for 4 h. Precipitated solids were filtered and washed with cold ethyl acetate and dried under high vacuum to afford the title compound as an off white solid (13.7 g, 59.6%). 1H NMR (DMSO-d6, 400 MHz): δ 3.905 (s, 3H), 7.754 (s, 1H), 8.183 (s, 1H), 10.274 (s, 1H), 14.563 (brs, 1H). LCMS (ES+): 281.06 [M−H] ion present.

Provenance & Evidence