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

Participants

Reaction Conditions

Reaction Steps

3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (5.9 g) was dissolved in DMF (120 ml). Potassium carbonate (27.6 g) and 1-bromo-2-chloroethane (9.99 ml) were added and heated at 50° C. for 18 hours. The reaction mixture was cooled to 40° C. and 2N NaOH (20 ml) was added and the mixture heated at 40° C. for 18 hours. The cooled reaction mixture was adjusted to pH 1 using concentrated hydrochloric acid to yield a brown oil. This oil was extracted with methylene chloride (×2), the organic solution was filtered through silicone treated filter paper (Whatman 1PS) and concentrated to yield 3-[7-(2-chloroethoxy)-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as a brown oil (6.59 g); NMR Spectrum: (DMSOd6) 2.22 (s, 1H), 3.85 (m, 2H), 4.40 (m, 2H), 6.60 (m, 1H), 6.95 (m, 1H), 7.40 (m, 1H), 7.46 (m, 1H), 7.56 (m, 1H), 7.90 (m, 1H), 7.95 (m, 1H); Mass Spectrum: M+H+ 358.

Provenance & Evidence