4-NITRO-PYRIDIN-2-YLAMINE Chemical Properties

Melting point:

96 °C

Boiling point:

339.0±22.0 °C(Predicted)

Density 

1.437±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

3.43±0.11(Predicted)

color 

Light yellow to orange

CAS DataBase Reference

4487-50-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

HS Code 

2933399990

4-NITRO-PYRIDIN-2-YLAMINE Usage And Synthesis

Uses

4-Nitropyridin-2-amine is used to synthesize tetrahydronaphthalene Raf inhibitors.

Synthesis

Step 3: Synthesis of 4-nitropyridine-2-amino intermediate-22 N-(4-methoxybenzyl)-4-nitropyridin-2-amine (Int-21, 27.8 g, 0.11 mol) and anisole (13 mL, 0.12 mol) were dissolved in trifluoroacetic acid (112 mL) and the reaction was heated at 80 °C for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated. The resulting residue was ground with EtOAc and hexane to give a pale yellow solid, which was separated by filtration. The filtrate was allowed to stand overnight to precipitate a second batch of crystals. The two solid batches were combined, dissolved in 1N NaOH solution (250 mL) and extracted with EtOAc (2 x 250 mL). The organic phases were combined, dried over magnesium sulfate, filtered and concentrated to give 4-nitropyridin-2-amine as an orange solid (10.2 g, 67% yield). LCMS (FA) ES+: m/z 140. 1H NMR (400 MHz, CD3OD) δ ppm: 8.15 (dd, J = 5.7, 0.6 Hz, 1H), 7.23 (dd, J = 2.0, 0.6 Hz, 1H), 7.20 (dd, J = 5.7, 2.0 Hz, 1H).

References

[1] Patent: WO2011/146591, 2011, A1. Location in patent: Page/Page column 72-73
[2] Patent: US2012/15942, 2012, A1. Location in patent: Page/Page column 51
[3] Patent: EP3305788, 2018, A1. Location in patent: Paragraph 0059; 0062
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 6, p. 1836 - 1846

4-NITRO-PYRIDIN-2-YLAMINE(4487-50-7)Related Product Information

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