Hydrochloric Acid → 2-(5-chloro-2H-benzo[d][1,2,3]triazol-2-yl)-6-(hydroxymethyl)-4-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

In a 500 ml round bottom flask equipped with a magnetic stirrer, addition funnel, powder addition funnel, and nitrogen inlet was added 27.4 g (81.0 mmol) 2-((5-chloro-2-nitrophenyl)diazenyl)-6-(hydroxymethyl)-4-methoxyphenol and 200 ml ethanol. NaOH (19.7 g, 493 mmol) was dissolved in 100 ml deionized water and approximately one-fourth was added dropwise to the reaction mixture. The mixture was heated to 80° C. and 26.5 g (245 mmol) formamidine sulfinic acid and the remaining sodium hydroxide solution were concurrently added dropwise to the reaction mixture. The mixture was stirred at 80° C. for 2 hours and then poured into 3 L deionized water. The mixture was acidified to pH 3 using 1N HCl and the solid was collected by filtration, rinsed with ample amounts of water, and then worked up as in Example 5 to afford 7.4 g (30%) solid which was used in the next esterification step.

Provenance & Evidence