Oxalyl chloride → HCID 56640372, compound

Participants

Reaction Steps

To an anhydrous tetrahydrofuran (10 mL) solution of oxalyl chloride (162 μL, 1.89 mmol) was dropwise added an anhydrous tetrahydrofuran (10 mL) solution of N2-(3-methoxyphenyl)naphthalene-1,2-diamine (500 mg, 1.89 mmol) under cooling in an ice-bath. The mixture was stirred under cooling in an ice-bath for 30 minutes and at room temperature for one hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and purified by silica gel chromatography (chloroform/methanol=97/3) after removing the solvent by evaporation under reduced pressure. The obtained solid was washed with ethyl acetate/methanol (=1/1) to obtain the titled compound as a slightly beige crystal (572 mg, yield 95%).

Provenance & Evidence