Oxalyl chloride → HCID 86655538, compound

Participants

Reaction Steps

Oxalyl chloride (129 μL, 1.50 mmol) and methylene chloride (3 mL) were added to a methylene chloride (2 mL) solution of 2-phenyl-6-trifluoromethoxy-4-quinolinecarboxylic acid (100 mg, 0.30 mmol) described in Reference Example 16, and the mixture was stirred at room temperature for 1 hour. After that, oxalyl chloride (129 μL, 1.50 mmol) was added, and the mixture was further stirred for 2 hours. The reaction solution was concentrated, and the residue was dissolved in anhydrous acetonitrile (1 mL). To the solution, potassium thiocyanate (146 mg, 1.50 mmol) was added, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, commercially available 2-thiophenecarbohydrazide (64 mg, 0.45 mmol) was added, and the mixture was stirred overnight at room temperature. To the reaction solution, methanol was added, and the mixture was concentrated. To the residue, a saturated aqueous solution of sodium chloride was added, and the deposited crystal was collected by filtration, washed with water, dried, and then purified by silica gel column chromatography to obtain the title compound (71 mg, 0.14 mmol).

Provenance & Evidence