Phosphorus oxychloride → HCID 86683003, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid (100 mg, 334 μmol, Eq: 1.00) and phosphorus oxychloride (3.29 g, 2 ml, 21.5 mmol, Eq: 64.3) was heated to 120° C. for 3 h. The reaction mixture was evaporated to dryness and the remaining residue was co-evaporated with toluene (2×). The residue was dissolved in DCM (1 ml) and 9-fluorenylmethyl carbazate (127 mg, 500 μmol, Eq: 1.5) was added. The reaction mixture was stirred at RT for 4 h. Then water was added and the mixture was extracted with ethyl acetate (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, DCM/EtOAc 9:1) to afford the title compound as off-white solid (102 mg). MS (ESI): 554.1 (M+H)+.

Provenance & Evidence