Methylamine → HCID 21876343, compound

Temperature

80 °C

To a solution of 2,4-dichloro-5-nitrobenzoic acid (8 g, 33.9 mmol) in toluene (200 ml) was added thionyl chloride (12.4 ml, 169 mmol) at room temperature. The mixture was stirred at 80° C. for 5 h. The solvent was removed and the residue was dissolved with tetrahydrofurane (60 ml). The mixture was added 40% methylamine (1.4 ml, 33.9 mmol) at 0° C. and the mixture was stirred at room temperature for 2.5 h. The volatile component was removed under reduced pressure, and the residue was extracted with ethyl acetate (100 ml). The organic layer was washed with water (100 ml), brine (100 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (2:1/1:1/1:2) to afford 5.3 g (63%) of the title compound as pale yellow solids.

1. customThe solvent was removed
2. dissolutionthe residue was dissolved with tetrahydrofurane (60 ml)
3. stirringthe mixture was stirred at room temperature for 2.5 h
4. customThe volatile component was removed under reduced pressure
5. extractionthe residue was extracted with ethyl acetate (100 ml)
6. washThe organic layer was washed with water (100 ml), brine (100 ml)
7. dry with materialdried (Na2SO4)
8. customAfter removal of solvent
9. customthe crude product was purified by flash column chromatography
10. washeluting with hexane/ethyl acetate (2:1/1:1/1:2)

ORD record

ord-ae850e2321f64c7d8ae092f65678a9d7

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148234B2