Methylamine → 6-chloro-N-methyl-3-nitropyridin-2-amine

Methylamine 2M in THF (67 mL, 134 mmol) was added to a stirred solution of 2,6-dichloro-3-nitropyridine (12, 93 g, 67 mmol) in THF (100 mL) at 0° C. and the resulting mixture was stirred at RT for 16 hr. The reaction was concentrated under reduced pressure; the residue was partitioned between water and EtOAc and both phases separated. The aq. layer was extracted with EtOAc, the combined organic layer were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (25% EtOAc/hexane) to afford the title product (10.54 g, 53.4 mmol, 80% yield) as yellow solid. tR: 0.96 min (LC-MS 2); ESI-MS: 187 [M+H]+ (LC-MS 2); Rf=0.72 (25% EtOAc/hexane).

1. concentrationThe reaction was concentrated under reduced pressure
2. customthe residue was partitioned between water and EtOAc
3. customboth phases separated
4. extractionThe aq. layer was extracted with EtOAc
5. washthe combined organic layer were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude material was purified by silica gel column chromatography (25% EtOAc/hexane)

ORD record

ord-f8c8f4dbbd124ea0875591e544fc730b

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975417B2