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

Participants

Reaction Conditions

Reaction Steps

In a 500 ml round bottom 3-neck flask equipped with a magnetic stirrer, addition funnel, powder addition funnel, and nitrogen inlet was added 2-(hydroxymethyl)-4-methoxy-6-((4-methoxy-2-nitrophenyl)diazenyl)phenol from Example 11 and 200 ml absolute ethanol (Pharmco Products, Brookfield, Conn.). NaOH pellets, 97% (Aldrich, 16.8 g, 420 mmol) were dissolved in 80 ml deionized water and approximately one-fourth of the solution was added dropwise to the azo mixture. The reaction mixture was heated to 80° C. and 22.6 g (209 mmol) formamidinesulfinic acid (Aldrich) and the remaining NaOH solution were added concurrently to the azo mixture over 0.5 hr. The mixture was heated at 80° C. for 3 hours, poured into 3.5 L water, and acidified to pH 4-5 with conc. HCl (J.T. Baker). The crude product was recrystallised from ethanol and then collected and vacuum dried (0.1 mm Hg) at 50° C. for 72 hours to give 7 g (27%) of a light yellow solid.

Provenance & Evidence