2-Methylamino-3-nitro-6-chloropyridine Chemical Properties

Melting point:

114 °C

Boiling point:

330 °C

Density 

1.489

Flash point:

153 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

-0.67±0.10(Predicted)

Appearance

White to yellow Solid

Safety Information

HS Code 

2933399990

2-Methylamino-3-nitro-6-chloropyridine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-methylamino-3-nitro-6-chloropyridine (9) from 2,6-dichloro-3-nitropyridine (8) (2.0 g, 10.4 mmol) and monomethylamine: 2,6-dichloro-3-nitropyridine (8) and sodium carbonate (2.75 g, 25.9 mmol) were suspended in ethanol (100 mL). Subsequently, methylamine solution (7.8 mL, 15.6 mmol, 2M) was added to the suspension and the resulting mixture was stirred and reacted for 3 hours at room temperature. Upon completion of the reaction, the yellow reaction solution was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed sequentially with sodium bicarbonate solution and saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting yellow solid was purified by recrystallization from ethanol to afford the target product 6-chloro-N-methyl-3-nitropyridin-2-amine (9) as a yellow solid (1.6 g, 82% yield). Mass spectrum (MS) m/z (M+H): calculated value=187.6; measured value=187.1. 1H NMR (400MHz, DMSO-d6): δ3.00 (3H, d, J=5.1Hz), 6.77 (1H, d, J=8.1Hz), 8.42 (1H, d, J=8.1Hz), 8.72 (1H, m).

References

[1] Journal of Medicinal Chemistry, 2000, vol. 43, # 16, p. 3052 - 3066
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 4, p. 1260 - 1264
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 3, p. 312 - 317
[4] Patent: US2014/349990, 2014, A1. Location in patent: Paragraph 1013; 1014
[5] Patent: WO2014/191896, 2014, A1. Location in patent: Page/Page column 209

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