Hydrochloric Acid → HCID 12557197, compound

Participants

Reaction Conditions

Reaction Steps

The amine prepared above (2.75 g, 13.8 mmol) was added to 2N HCl (20 mL), then cooled to 5° C., giving a thick purple slurry. A solution of sodium nitrite (0.84 g, 14.2 mmol) in water (2 mL) was added dropwise, keeping the reaction temperature -5° C. Addition of another small portion of sodium nitrite to the reaction resulted in a positive HONO test with a Kl-starch strip, so the pH was adjusted to 7-8 using solid Na2CO3. This solution was added in portions to a vigorously stirred mixture of toluene (10 mL) and a solution of sodium cyanide (1.65 g, 33.6 mmol) and copper(I) cyanide (1.45 g, 16.2 mmol) in water (15 mL), keeping the reaction temperature -5° C. The very thick, brown reaction mixture was diluted with more toluene, stirred at 5° C. for 15 minutes, then at room temperature for 2 hours. The reaction mixture was added to EtOAc and 2N HCl; the organic layer was dried with Na2SO4 and concentrated in vacuo. The residue obtained was chromatographed eluting with 95:5 hexane-Et2O to give the title compound as an orange-red oil (500 mg, 17%). 1H NMR (CDCl3) δ 7.55 (d, 1H), 7.40 (m, 3H), 7.20 (m, 1H), 7.00 (m, 2H), 6.79 (d, 1H), 2.35 (s, 3H). MS (DCl/NH3) m/e 227 (M+H+NH3)+.

Provenance & Evidence