Ammonia → 8-Quinolinesulfonamide

Participants

Reaction Conditions

Reaction Steps

Quinoline-8-sulfonyl chloride (1.0 g, 4.39 mmol) was slurried into DCM (20 mL) and cooled to −60° C. Then ammonia (˜5 g, 294 mmol) was bubbled into the reaction over 5 min (volume increased by ˜5 mL). The reaction was stirred and allowed to come to rt overnight. The residue was partitioned between water (50 mL) and EtOAc (50 mL) and the organic layer was washed with brine (20 mL) and diluted with hexanes (˜50 mL). The solution was stirred 20 min and the solids were collected by filtration to yield quinoline-8-sulfonamide (432 mg, 2.07 mmol, 47% yield) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.25 (s, 2H), 7.73 (dd, J=8.3, 4.3 Hz, 1H), 7.76 (dd, J=8.6, 7.3 Hz, 1H), 8.28 (d, J=8.3 Hz, 1H), 8.31 (d, J=7.3 Hz, 1H), 8.56 (br d, J=8.6 Hz, 1H), 9.08 (dd, J=4.3, 0.9 Hz, 1H). LC-MS retention time: 1.27 min; m/z 209 (MH+). LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Phenomenex-Luna 10 u C18 4.6×50 mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 5 mL/min, a gradient of 100% solvent A/0% solvent B to 0% solvent A/100% solvent B, a gradient time of 4 min, a hold time of 1 min, and an analysis time of 5 min where solvent A was 5% acetonitrile/95% H2O/10 mM ammonium acetate and solvent B was 5% H2O/95% acetonitrile/10 mM ammonium acetate. MS data was determined using a Micromass Platform for LC in electrospray mode.

Provenance & Evidence