Morpholine → (3,4-Dinitrophenyl)(morpholino)methanone

A solution of 3,4-dinitrobenzoic acid (10 g, 47 mmol, 1 eq.) and DMF (0.1 mL) in THF (100 mL) was treated with thionyl chloride (4.5 mL, 62 mmol, 1.3 eq.) then heated to reflux for 2.5 h. The mixture was cooled in ice then triethylamine (10 mL, 71 mmol, 1.1 eq.) was added over 20 min, keeping internal temperature <5° C. Morpholine (6.2 mL, 71 mmol, 1.5 eq) was added to the resulting thick yellow suspension over 15 min, keeping internal temperature <10° C. The ice-bath was removed and the mixture allowed to warm to r.t. After 15 min, a further portion of morpholine (1 mL, 11 mmol, 0.24 eq.) was added and the mixture stirred overnight. The mixture was diluted with water (250 mL) and cooled in ice. A beige solid was filtered off under suction, washed with a further portion of cold water (25 mL) and dried in vacuo to afford the title compound (12.7 g, 96%).

1. temperaturethen heated
2. temperatureto reflux for 2.5 h
3. temperatureThe mixture was cooled in ice
4. customtemperature <5° C
5. customtemperature <10° C
6. customThe ice-bath was removed
7. temperaturecooled in ice
8. filtrationA beige solid was filtered off under suction
9. washwashed with a further portion of cold water (25 mL)
10. customdried in vacuo

ORD record

ord-24422cd6aebf43c7b69521d14eed46cb

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399442B2