Hydrochloric Acid → HCID 178493285, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL round bottom flask charged with a magnetic stir bar and 1-(2-amino-4,5-dimethoxyphenyl)ethanone (1.23 g, 6.29 mmol) was added water (4 mL). The mixture was cooled to 0° C. with an ice bath and concentrated aqueous HCl (1.95 mL) was added to the reaction mixture. With efficient stirring, a solution of sodium nitrite (0.434 g, 6.9 mmol) in water (3 mL) was added to the reaction mixture via Pasteur pipette. The reaction was allowed to stir for 5 minutes at this temperature followed by the slow addition of a solution of pyrrolidine (0.447 g, 6.30 mmol) in 50 mL of 0.4 N aqueous potassium hydroxide. The reaction was allowed to stir at this temperature for 0.5 h before being poured into a separatory funnel and extracted with DCM (2×100 mL). The combined organic extract was dried with MgSO4, filtered, and concentrated in vacuo to yield the crude product which was purified on 80 g of silica using hexanes/EtOAc (1:1) as eluent to give 1.49 g (85%) of the title compound as a brown solid. 1H NMR: 7.12 (s, 1H), 7.01 (s, 1H), 3.92 (m, 2H), 3.80 (s, 3H), 3.75 (s, 3H), 3.58 (m, 2H), 2.60 (s, 3H), 2.00 (M, 4H); m/z: 278.

Provenance & Evidence