Sodium Bicarbonate → HCID 178433788, compound

Participants

Reaction Steps

3-Amino-3′-(1H-tetrazol-5-yl)-biphenyl-2-ol hydrochloride 8f (188 mg, 0.74 mmol) was dissolved in 4 mL of 2 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 1 mL of aqueous sodium nitrite (57 mg, 0.82 mmol). After the mixture was reacted for 30 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (159 mg, 0.74 mmol) was added. The mixture was adjusted to pH 8 with saturated sodium bicarbonate, followed by addition of 0.5 mL of ethanol. The reaction mixture was reacted overnight at room temperature. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in aqueous sodium hydroxide (3 N). The mixture was washed three times with dichloromethane. The layers were separated and then the aqueous layer was adjusted to pH 3 with 2 N hydrochloric acid to form a copious amount of precipitates. The mixture was filtered and the filter cake was purified by silica gel column chromatography to obtain the title compound 4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)-biphenyl-3-yl]-hydrazono}-2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 27 (67 mg, yield 18.8%) as an orange solid.

Provenance & Evidence