Hydrochloric Acid → HCID 178434044, compound

Participants

Reaction Conditions

Reaction Steps

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.233 g, 0.571) and ethyl formate (0.140 mL, 1.71 mmol) were dissolved in anhydrous ethanol (1.10 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (1.10 mL, 2.85 mmol). This reaction mixture was heated at 78° C. for 1 h, turning the reaction mixture to a brownish red color. The reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 1 with dropwise addition of 1M HCl(aq) causing the formation of a pale brown precipitate. The suspension was filtered yielding a tan solid as pure 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (0.147 g, 0.337 mmol, 59%).

Provenance & Evidence