Sulfuric Acid → 1-amino-4-nitroisoquinoline H2SO4

Participants

Reaction Conditions

Reaction Steps

Cool sulfuric acid (900 mL) to 5° C. using an ice/acetone bath, then add 1-aminoisoquinoline (208.8 g, 1448 mmol) over 45 min keeping the internal temperature of the mixture <20° C. Cool the dark mixture to 0° C. under nitrogen with mechanical stirring then treat with KNO3 (149.4 g, 1477 mmol) in portions over 45 min keeping the reaction mixture's temperature <10° C. Stir the mixture for 2 hours while warming to 15° C. Pour the mixture into water/ice (3 kg) then dilute with additional water (6 L). Stir the slurry for 45 min then filter. Wash the cake with water (6×1.5 L). Partially dry the golden material by air overnight then place in a vacuum oven (50-55° C., ca. 10 torr, nitrogen bleed, 24 h) to afford 1-amino-4-nitroisoquinoline H2SO4 (256.8 g, 62% yield). (ES+): m/z 190 (M++H).

Provenance & Evidence