5-METHOXY-2-(1H-PYRROL-1-YL)ANILINE Chemical Properties

Melting point:

41-43°C

Boiling point:

345.3±32.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

2.05±0.11(Predicted)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

2933998090

5-METHOXY-2-(1H-PYRROL-1-YL)ANILINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-methoxy-2-(1H-pyrrol-1-yl)aniline from 1-(4-methoxy-2-nitrophenyl)-1H-pyrrole: a methanolic (10 mL) suspension of 1-(4-methoxy-2-nitrophenyl)-1H-pyrrole (3 mmol) and palladium carbon (10%, 60 mg) was stirred for 5 hours under the atmosphere of hydrogen balloon. Upon completion of the reaction, the black solid was removed by filtration and the filtrate was concentrated to afford the crude product of 5-methoxy-2-(1H-pyrrol-1-yl)aniline. The crude product was purified by fast silica gel column chromatography (eluent: ethyl acetate-hexane, gradient to 1:4) to afford the target product as a light yellow oil (97% yield).1H NMR (400 MHz, CDCl3) δ 7.13-7.09 (m, 1H), 6.83-6.82 (m, 2H), 6.40-6.37 (m, 4H), and 3.84 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 159.9, 143.4, 128.2, 122.1, 121.2, 109.2, 103.6, 101.1, 55.4.

References

[1] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4511 - 4525
[2] Patent: WO2017/149493, 2017, A1. Location in patent: Page/Page column 0150; 0151
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 1997 - 2009
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 52, p. 14451 - 14455
[5] Angew. Chem., 2014, vol. 126, # 52, p. 14679 - 14683,5

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