Ammonia → HCID 18382576, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of potassium nitrate (2.53 g) in sulfuric acid (14 ml ) at 0° C. was added dropwise a solution of 3,4-dihydro-3,3-dimethyl isoquinoline (3.68 g; 23 mmol) [prepared according to the procedure of T. J. N. Watson, J. Org. Chem., 1998, 63, 406] in sulfuric acid (13.5 ml). The resultant solution was stirred at room temperature for 1.5 h and then heated to 60° C. for 4.5 h. The solution was then cooled to room temperature, and poured on to ice.; 0.880 ammonia was added until the solution was neutral, and the product was extracted into dichloromethane (×3). The combined organic phases were, dried over magnesium sulphate, and then evaporated in vacuo to afford the title compound (4.22 g). 1H NMR (CDCl3)δ: 1.27 (6H, s), 2.85 (2H, s), 7.34 (1H, d, J=8 Hz), 8.17 (1H, d, J=2Hz), 8.23 (1H, dd, J=8, 2Hz), 8.33 (1H, s).

Provenance & Evidence