Ammonia → 2-(Isoquinolin-8-YL)acetic acid

Participants

Reaction Steps

To a solution of tert-butyl 2-(isoquinolin-8-yl)acetate (1.8 g) in DCM (10 mL) was added TFA (10 mL) dropwise. The reaction was stirred at room temperature overnight. After the reaction was complete, the solvent was removed to give a residue which was adjusted to pH 3-4 with aqueous ammonia. The precipitate was filtered off and washed with water. The final product was purified (silica gel coulumn chromatography) to afford 2-(isoquinolin-8-yl)acetic acid as a solid (1.2 g, 87%). LC-MS (0.05% TFA): [M+1]+ 188.1. 1H-NMR (DMSO-d6, 400MHz): δ13.0 (brs, 1H), 9.65(s, 1H), 8.61(d, 1H, J=4.8Hz), 8.16 (d, 1H, J=4.8Hz), 8.05 (d, 1H, J=6.8Hz), 7.92 (t, 1H), 7.72 (d, 1H, J=6.8Hz), 4.29 (s, 2H).

Provenance & Evidence