Ammonia → 8-Fluoroisoquinoline

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-6-(2-(trimethylsilyl)ethynyl)benzaldehyde (2.3 g, 10.5 mmol) was dissolved in ammonia (2M in methanol, 15 mL, 30 mmol) and the resulting mixture was heated at 80° C. in a sealed tube for 2.5 h. The solvent was removed under high vacuum and the resulting crude product purified by silica gel chromatography (20-30% EtOAc in hexanes) to give 8-fluoroisoquinoline as a pale yellow solid. MS (ESI, pos. ion) m/z: 148 (M+1).

Provenance & Evidence