Sodium Hydroxide → HCID 178426116, compound

Participants

Reaction Conditions

Reaction Steps

Sodium azide (395 mg, 6.1 mmol) and ammonium chloride (325 mg, 6.1 mmol) are added to a solution of {4-chloro-2-methyl-6-[3-(quinolin-2-ylmethoxy)-phenoxymethyl]-phenoxy}-acetonitrile (300 mg, 0.68 mmol, example 36c) in DMF (2 mL) and heated at 110° C. for 2 h. The reaction is then cooled and poured into a 1 N sodium hydroxide solution (20 mL) with the formation of a solid. This mixture is then washed with ether (4×) and the ether is discarded. The remaining aqueous solution contains a solid which is filtered. This solid is dissolved in 10% ethanol water (250 mL) and the pH is lowered to about 5 with 2N HCl. A solid precipitates which is filtered to provide the title compound. m.p. 181–184° C.; 1H NMR (300 MHz, DMSO-d6) d 8.40 (d, 1H), 8.01–7.97 (m, 2H), 7.77 (dd, 1H), 7.66–7.60 (m, 2H), 7.33 (d, 2H), 7.18 (dd, 1H), 6.72 (dd, 1H), 6.65 (dd, 1H), 6.59 (dd, 1H), 5.33 (s, 2H), 5.27 (s, 2H), 5.07 (s, 2H), 2.24 (s, 3H); MS (EST) 488, 490 (M+H;Cl)+.

Provenance & Evidence