Sodium Bicarbonate → HCID 178433821, compound

Participants

Reaction Steps

4-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid 22e (170 mg, 0.57 mmol) was dissolved in hydrochloric acid (1.9 mL, 1 M) upon cooling by an ice-water bath, followed by dropwise addition of 0.7 mL of sodium nitrite solution (43 mg, 0.63 mmol). After the mixture was reacted for 20 minutes, 5-methyl-2-(5,6,7,8-tetrahydro-naphthalen-2-yl)-2,4-dihydro-pyrazol-3-one 7c (116 mg, 0.51 mmol) was added. The mixture was adjusted to pH 8-9 with saturated sodium bicarbonate solution followed by addition of 2 mL of ethanol. The mixture was reacted at room temperature for 24 hours. The mixture was filtered and then 15 mL of water was added to the filter cake. Upon cooling by an ice-water bath, the mixture was adjusted to pH 2-3 with concentrated hydrochloric acid and filtered. The filter cake was washed with ethyl acetate and dried to obtain the title compound (Z)-4-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthal-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-furan-2-carboxylic acid 22f (13 mg, yield 5.5%) as a red solid.

Provenance & Evidence