Sodium Bicarbonate → HCID 178433837, compound

Participants

Reaction Steps

(Z)-5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 4g (333 mg, 1.1 mmol) was dissolved in hydrochloric acid (3.7 mL, 1 M) upon cooling by an ice-water bath, followed by dropwise addition of 1.5 mL of sodium nitrite solution (85 mg, 1.22 mmol). After the mixture was reacted for 20 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 4c (242 mg, 1.0 mmol), sodium bicarbonate (1.4 g, 16.67 mmol) and 3 mL of ethanol were added successively. The reaction mixture was reacted overnight at room temperature. The mixture was filtered and 20 mL of water was added to the filter cake. The mixture was adjusted to pH 3-4 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried and purified by silica gel column chromatography to obtain the title compound (Z)-5-(3-{N′-[1-(3,3-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2-hydroxy-phenyl)-furan-2-carboxylic acid 4h (190 mg, yield 40.3%) as a red solid.

Provenance & Evidence