Nitric Acid → 6-Methoxy-7-nitro-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(methyloxy)-3,4-dihydro-1(2H)-isoquinolinone (3.4 g, 17.8 mmol) in H2SO4 (45 mL) at −20° C. was added HNO3 (1.58 mL, 21.3 mmol) dropwise. The mixture was allowed to stir for 3 h at −20° C. The mixture was poured into ice water and the aqueous layer was extracted with dichloromethane. The combined organic layers were concentrated under reduced pressure to give 6-(methyloxy)-7-nitro-3,4-dihydro-1(2H)-isoquinolinone (3.0 g, 71%). 1H NMR (CDCl3) δ 8.55 (1H), 6.88 (1H), 6.2 (1H), 4.0 (3H), 3.6 (2H), 3.05 (2H).

Provenance & Evidence