Hydrochloric Acid → HCID 59549116, compound

Participants

Reaction Steps

Compound 22 (12.00 g, 50.36 mmol) was added to H2O (50.0 mL) and concentrated HCl (100 mL) at room temperature. The reaction mixture was then stirred in an ice bath. Sodium nitrite (10.434 g, 151.1 mmol) in H2O (50 mL) was added to the reaction mixture dropwise at 0° C. The reaction mixture was allowed to stir in the ice bath for an hour. In a separate flask, sulfur dioxide was bubbled through acetic acid (430 mL) for 45 min. Cupric chloride dihydrate (4.305 g, 25.2 mmol) was then added to this sulfur dioxide saturated solution, and stirred for an additional 30 min. This saturated sulfur dioxide solution was then stirred in an ice bath for an additional five min. The reaction mixture containing compound 22 was then added dropwise to the cupric chloride solution. After the addition was complete, the solution was stirred for an additional hour and then poured slowly onto an ice water slurry and stirred for an hour. The resulting precipitate was then filtered and the yellow solid was rinsed with water to afford compound 23 (13.944 g, 86.1% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.06 (d, J=2 Hz, 1H), 7.71 (dd, J1=8 Hz, J2=2 Hz, 1H), 6.85 (s, 1H), 6.81 (d, J=9 Hz, 1H), 6.66 (s, 2H), 2.26 (s, 6H).

Provenance & Evidence