Sodium Carbonate → HCID 22877459, compound

Participants

Reaction Steps

To a solution of 440 mg (2.50 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Example 1, Step E) in 5 mL of concentrated sulfuric acid at 0° C. was added 265 mg (2.63 mmol) of potassium nitrate. The resulting yellow solution was stirred for 30 minutes at then at room temperature for 24 hours. The reaction mixture was poured carefully into 100 g of ice and the pH of the resulting mixture was adjusted to 11 by the portionwise addition of sodium carbonate. The mixture was transferred to a separatory funnel and extracted thoroughly with ethyl acetate (4×100 mL). The organic extracts were combined, washed with brine (100 mL), dried over sodium sulfate and filtered. The solvent was removed under vacuum to afford 385 mg (70%) of the product as a yellow solid. 1H NMR (200 MHz, CDCl3): δ 1.58 (s, 2H), 1.98 (m, 1H), 2.47-2.70 (m, 1H), 2.72-3.05 (m, 2H), 3.40 (dd; 11, 8 Hz; 1H), 7.07 (d, 8 Hz, 1H), 7.92 (s, 1H), and 8.10 (m, 1H). FAB-MS: calculated for C10H11N3O3 221; found 222 (M+H,100%).

Provenance & Evidence