Sodium Hydroxide → HCID 178423905, compound

Participants

Reaction Steps

16.4 g of titanium tetrachloride was added to a stirred solution of 22.5 g of 53C in 160 ml of chlorobenzene, under nitrogen, at 20° C. The mixture was heated at 90°-100° C. for 5 hours and let stand over a weekend at room temperature. Then 20 ml of a solution of 26.4 g of sodium hydroxide in 330 ml of water was added, drop-by-drop, and the mixture was stirred well and stripped of solvent to form a mush. The remainder of the sodium hydroxide solution was added, and the mixture was stirred and filtered through Celite. The filtrate was acidified with 12 N hydrochloric acid and filtered. The solid was dried under reduced pressure and dissolved in 150 ml of 2 N aqueous ammonium hydroxide solution. The solution was filtered. The filtrate was acidified with 12 N hydrochloric acid and filtered. The solid was washed with water, dried under reduced pressure and dissolved in warm ethanol. The solution was filtered and the solvent was evaporated from the filtrate, to give 8-methyl-4-hydroxy-cinnoline-3-carboxylic acid (53D), as a solid, m.p.: 230° C. (with decomposition).

Provenance & Evidence