Morpholine → HCID 67508051, compound

Participants

Reaction Conditions

Reaction Steps

To a flask containing 4-amino-2-chloro-5-iodobenzonitrile (1 g, 3.6 mmol) in DMSO (5.0 mL) was added morpholine (1.0 mL, 11.5 mmol) dropwise. Upon complete addition, the mixture was warmed to 100° C. After 40 h, the reaction mixture was cooled to rt, then an additional 2 mL of morpholine was added to the mixture. The reaction was re-heated to 100° C. and monitored with LC-MS. After 17 h, the reaction was cooled to rt, then 1 g of potassium carbonate was added in portions. The reaction was re-heated to 100° C. and monitored with LC-MS. After 13 days, the reaction was diluted with water then subsequently extracted five times with EtOAc. The organic extractions were then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-35% EtOAc in hexanes) to afford a pale brown solid as 4-amino-5-iodo-2-morpholinobenzonitrile. 1H NMR (500 MHz, CDCl3) δ ppm 7.80 (1H, m), 6.27 (1H, s), 4.57 (2H, br. s.), 3.92 (4H, m), 3.20 (4H, m). Mass Spectrum (pos.) m/e: 330.0 (M+H)+.

Provenance & Evidence