Morpholine → HCID 18377044, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(5-chloropyridin-2-yl)-2-nitro-3,5-dichlorobenzamide (12 g, 34 mmol) in DMSO (50 mL) was added morpholine (3.6 g, 41 mmol) followed by N,N-diisopropylethylamine (8.9 g, 69 mmol). The mixture was heated at 110-120° C. for 4 hours, then cooled to ambient temperature, quenched with water (50 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine (2×30 mL), dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 6.3 g (46% yield) of N-(5-chloropyridin-2-yl)-2-nitro-3-(morpholin-4-yl)-5-chlorobenzamide; NMR (CDCl3) 8.2 (m, 1), 7.7 (m, 1), 7.2-7.4 (m, 3), 3.8 (m, 4), 3.0 (m, 4) ppm.

Provenance & Evidence