2-Methylamino-3-nitro-6-chloropyridine

2, 6-Dichloro-3-nitropyridine(8) (2.0 g, 10.4 mmol) and sodiumcarbonate (2.75 g, 25.9 mmol) were suspended in ethanol (100 mL). Methylamine in methanol (7.8 mL, 15.6 mmol, 2M) was then added and the resulting mixture stirred at room temperature for 3h. The yellow solution was concentrated in vacuo and then re-dissolved in ethylacetate followed by washing with sodium bicarbonate and brine. The organic phase was dried over sodiumsulfate, filtered and concentrated invacuo. The yellow solid was thenre-dissolved in ethanol and recrystallized to give 6-chloro-N-methyl-3-nitropyridin-2-amine (9) as a yellow solid (1.6 g, 82percent). MS m/z(M+H): calculated = 187.6; observed = 187.1. Step 102.1: 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 NaMethylamine 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 00 and the resulting mixture was stirred at RT for 16 hr. The reaction was concentrated under reduced pressure; the residue waspartitioned 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 Na2504, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (25percent EtOAc/hexane) to afford the title product (10.54 g, 53.4 mmol, 80percent yield) as yellow solid. tR. 0.96 mm (LC-MS 2); ESl-MS: 187 [M+H] (LC-MS 2); R = 0.72 (25percentEtOAc/hexane).To a solution of 2, 6-dichloro-3-nitropyridine (1 g, 7.3 mmol) in EtOH (10 mL) was added Na

Molecular Weight:187.58
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:187.0148541
Monoisotopic Mass:187.0148541
Topological Polar Surface Area:70.7
Heavy Atom Count:12
Complexity:173
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes