Sodium Bicarbonate → HCID 178433818, compound

Participants

Reaction Steps

5-(2-Hydroxy-3-amino-phenyl)-2-methyl-furan-3-carboxylic acid hydrobromide 53e (200 mg, 0.64 mmol) was dissolved in 2.2 mL of 1 N hydrochloric acid upon cooling by an ice-water bath, followed by dropwise addition of 0.9 mL of aqueous sodium nitrite (48 mg, 0.7 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 3i (131 mg, 0.57 mmol) was added. The mixture was adjusted to pH 8 with saturated aqueous sodium bicarbonate followed by addition of 2 mL 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 added to 20 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid. The mixture was filtered and 8 mL of ethyl acetate was added to the filter cake. After stirring for 1 hour, the mixture was filtered and the filter cake was dried to obtain the title compound 5-(2-hydroxy-3-{N′-[3-methyl-5-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-phenyl)-2-methyl-furan-3-carboxylic acid 53 (200 mg, yield 73.8%) as a red solid.

Provenance & Evidence