Hydrochloric Acid → 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

Participants

Reaction Steps

Methyl 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoate (176 mg) was stirred in a solution of methanol (2 ml) and 1N NaOH solution (0.57 ml) at 65° C. for 1 hour and then neutralised with 2N HCl (0.28 ml). The reaction mixture was concentrated and the residue was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to yield 3-[7-[3-(dimethylamino)propyl]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as a cream coloured solid (155 mg); NMR Spectrum: (DMSOd6) 1.81 (m, 2H), 2.12 (s, 3H), 2.24 (s, 6H), 2.38 (t, 2H), 2.76 (t, 2H), 6.71 (d, 1H), 7.29 (d, 1H), 7.51 (d, 1H), 7.66 (m, 2H), 7.76 (s, 1H), 7.94 (d, 1H), 8.08 (s, 1H); Mass Spectrum: M+H+ 365.

Provenance & Evidence