Potassium Hydroxide → N-(7-hydroxyisoquinolin-3-yl)cyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask was charged with N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (3.0058 g, 10.324 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (0.1843 g, 0.1780 mmol), and 2-di-t-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-tri-1-propylbiphenyl (0.2514 g, 0.5229 mmol). The flask was evacuated and backfilled with nitrogen five times and then 1,4-dioxane (10 mL, 200 mmol) and potassium hydroxide (2.413 g, 43.01 mmol) dissolved in water (10 mL, 800 mmol) were added. The reaction mixture was heated at 90° C. under a nitrogen balloon for 2 hours. The reaction mixture was then cooled to room temperature and poured into 150 mL water. The resulting precipitate was filtered, rinsed with water, and dried under vacuum to yield 1.7974 g (76%) of N-(7-hydroxyisoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): M+H=229.2; 1H NMR (400 MHz, DMSO-d6) δ 10.67 (s, 1H), 9.90 (s, 1H), 8.91 (s, 1H), 8.32 (s, 1H), 7.71 (d, J=8.9 Hz, 1H), 7.27 (dd, J=8.9, 2.3 Hz, 1H), 7.22 (s, 1H), 2.13-1.95 (m, 1H), 0.91-0.70 (m, 4H).

Provenance & Evidence