Nitric Acid → 1-methyl-5-nitroIsoquinoline

Participants

Reaction Conditions

Reaction Steps

A solution 1-methylisoquinoline (D91) (1 g, 7 mmol) in sulfuric acid (2.5 ml) was cooled (<4° C.) and concentrated nitric acid (1 ml) was added over 10 mins. The reaction was stirred for 30 mins and then heated at 60° C. for 2 h. After cooling, the reaction mixture was poured into ice water slurry (100 ml) and basified using solid potassium carbonate followed by extraction with DCM. The organic phase was separated, dried over MgSO4, filtered and concentrated in vacuo to afford the product as a white solid (1.05 g). 1H NMR (400 MHz, DMSO) δ (ppm): 8.69 (d, 1H), 8.59 (m, 2H), 8.11 (d, 1H), 7.88 (t, 1H), 2.99 (s, 3H).

Provenance & Evidence