Sodium Iodide → 4-Methyl-3-[7-(2-morpholin-4-ylethoxy)-1-oxoisoquinolin-2(1H)-yl]benzoic acid

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3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (885 mg) was dissolved in acetone (50 ml), sodium iodide (45 mg) and potassium carbonate (4.14 g) were added followed by 4-(2-chloroethyl) morpholine hydrochloride (1.68 g). The resultant mixture was stirred at 60° C. for 18 hours. 2N NaOH (9.4 ml) was added and stirred for 20 minutes, cooled and the insoluble material removed by filtration. The filtrate was concentrated, acidified to pH 1 with concentrated hydrochloric acid and 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 give 4-methyl-3-[7-(2-morpholin-4-ylethoxy)-1-oxoisoquinolin-2(1H)-yl]benzoic acid as an oil (720 mg); NMR Spectrum: (DMSOd6) 2.00 (s, 1H), 2.60 (m, 4H), 2.80 (m, 2H), 3.18 (m, 4H), 3.75 (m, 2H), 6.40 (d, 1H), 6.80 (d, 1H), 7.03 (d, 1H), 7.20 (m, 1H), 7.40 (d, 1H), 7.75 (m, 3H); Mass Spectrum: M+H+ 409.

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