Toluene → HCID 19038242, compound

Participants

Reaction Steps

Indole-2-carboxylic acid (1.35 g, 8.38 mmol), oxalyl chloride (4 mL), and DMF (3 drops) were added in order to 50 mL toluene, and stirred until gas evolution subsided and a homogeneous solution was obtained (c.20 min). Solvent was removed in vacuo, the residue taken up in CH2Cl2, and added to a solution of 4,5-diphenyl-3-pyrazolidinone (2.0 g, 8.40 mmol, 1.00 eq.) in 50 mL CH2Cl2 and 5 mL pyridine. After stirring overnight, the solution was washed with 1N HCl, dried over Na2SO4, and solvent removed in vacuo. The residual solid was stirred with CH2Cl2, filtered, and recrystallized from DMF:H2O to give 1.42 g (44%) white solid: mp 248°-50° C.

Provenance & Evidence