Sodium Bicarbonate → HCID 178433840, compound

Participants

Reaction Steps

5-(3-Amino-2-hydroxy-phenyl)-thiophene-2-carboxylic acid 12c (171 mg, 0.62 mmol) was dissolved in 3 mL of hydrochloric acid (1 N) upon cooling by an ice-water bath, followed by dropwise addition of 1 mL of aqueous sodium nitrite (47 mg, 0.68 mmol). After the mixture was stirred for 20 minutes, 2-(3,3-dimethyl-indan-5-yl)-5-methyl-2,4-dihydro-pyrazol-3-one 8i (150 mg, 0.62 mmol) was added. The mixture was adjusted to pH 8-9 by batch addition of aqueous sodium bicarbonate (781 mg, 9.3 mmol). The generated bubbles were quenched with 2 mL of ethanol and the mixture was warmed up to room temperature and stirred overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was filtered and the filter cake was dissolved in 20 mL of water. The mixture was adjusted to pH 3˜4 with concentrated hydrochloric acid, filtered and dried. The crude product was purified by HPLC to obtain the title compound 5-(3-{N′-[1-(3,3-dimethyl-indan-5-yl)-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene]-hydrazino}-2-hydroxy-phenyl)-thiophene-2-carboxylic acid 12 (48 mg, yield 15.9%) as an orange solid.

Provenance & Evidence