Trifluoroacetic acid → HCID 178433876, compound

Participants

Reaction Conditions

Reaction Steps

2-(3,4-Dimethylphenyl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one (2.0 g, 4.29 mmole) was suspended in ethanol (17 ml) and water (1.85 ml). The brown slurry was treated with choline hydroxide (2.68 ml, 2.2 eq) (supplied as a 45% wt solution in methanol) at ambient temperature to form a deep purple solution which was stirred for 30 mins. The solution was filtered, and rinsed through with ethanol (4 ml). Triflouroacetic acid (0.36 ml, 1 eq) in water (1.85 ml) was added to the filtrate to form an orange-red slurry which was then heated to 78° C. (reflux) and stirred for 30 mins. The reaction was then cooled to 60° C. and treated with ethanol (25 ml, 12.5 vol) and stirred for a further 1 h at 60° C. The suspension was then cooled to ambient and stirred for 17 h. After filtration the cake was washed with ethanol (8 ml, 4 vol). The resulting solid was dried at 50° C. in vacuo to give 2-(3,4-dimethylphenyl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one choline as an orange solid (2.02 g, 83%).

Provenance & Evidence