Hydrochloric Acid → HCID 178493321, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-cyano-7-fluoro-4-hydroxy-5-[(1-methylpiperidin-4-yl)oxy]quinoline (600 mg), methanol (0.40 ml) and potassium tert-butoxide (1.0M solution in tetrahydrofuran; 10.0 ml) in anhydrous dimethyl sulphoxide (20 ml) was heated at 70° C. for 16 hours. The solution was cooled and then diluted with water (100 ml). Dilute hydrochloric acid was added until pH6 was reached and the by-product precipitate (3-cyano-4-hydroxy-5,7-dimethoxyquinoline) was filtered off. The filtrate was pumped onto a cation exchange cartridge (Waters Oasis MCX 6.0 g) and washed on with water. The column was flushed successively with water (200 ml), methanol/water (1:1; 200 ml) and methanol (200 ml). The product was eluted off the column with methanol containing triethylamine (1%). The fractions containing the product were combined and evaporated. This gave the title compound as an white solid (460 mg, 73%); NMR spectrum: (DMSOd6) 1.67 (m, 2H), 1.83 (m, 2H), 2.12 (m, 2H), 2.15 (s, 3H), 2.64 (m, 2H), 4.31 (m, 1H), 6.31 (d, 1H), 6.56 (d, 1H), 8.16 (s, 1H); Mass spectrum: M+H+ 314.

Provenance & Evidence