Sulfuric Acid → 7-Bromoisoquinolin-3-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-amino-7-bromoisoquinoline-4-carbonitrile (25 g, 101 mmol) in water (100 mL) was added H2SO4 (100 mL) dropwise while cooling in an ice-water bath. Then the mixture was stirred and heated to 115° C. for 3 days. After that, the reaction was cooled down to 0° C. 10 M aqueous NaOH was added to adjust to pH>12. The resulting solid precipitate was collected by filtration, washed with water, and dried under vacuum to yield 4.2 g (19%) of 7-bromo-isoquinolin-3-amine. LCMS (ESI): M+H=222.8; 1H NMR (400 MHz, DMSO-d6) δ 8.76 (s, 1H), 8.00 (t, J=0.8 Hz, 1H), 7.49-7.48 (m, 2H), 6.58 (s, 1H), 6.06 (s, 1H).

Provenance & Evidence