Sodium Bicarbonate → HCID 178433834, compound

Participants

Reaction Steps

3-Amino-3′-(1H-tetrazol-5-yl)-biphenyl-2-ol hydrochloride 8f (290 mg, 1.0 mmol) was dissolved in hydrochloric acid (3.4 mL, 1 mol/L) followed by dropwise addition of 1.2 mL of aqueous sodium nitrite (73 mg, 1.05 mmol) upon cooling by an ice-water bath. After the mixture was reacted at room temperature for 10 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (218 mg, 0.9 mmol), sodium bicarbonate (1.26 g, 15 mmol) and 4.4 mL of ethanol were added successively. Then the reaction mixture was reacted for 10 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was washed with 20 mL of water and then dissolved in 20 mL of water. Upon cooling by an ice-water bath, the mixture was adjusted to pH<5 with concentrated hydrochloric acid. The mixture was filtered and dried to obtain the title compound 2-(3,3-dimethyl-indan-5-yl)-4-{[2-hydroxy-3′-(1H-tetrazol-5-yl)-biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydro-pyrazol-3-one 8 (336 mg, yield 73.8%) as a yellow solid.

Provenance & Evidence