3-chloro-4-(pyridin-2-ylmethoxy)aniline Chemical Properties

Melting point:

91.0 to 95.0 °C

Boiling point:

402.5±35.0 °C(Predicted)

Density 

1.292±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

3.88±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C12H11ClN2O/c13-11-7-9(14)4-5-12(11)16-8-10-3-1-2-6-15-10/h1-7H,8,14H2

InChIKey

XCAPJQSICQSUJP-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(OCC2=NC=CC=C2)C(Cl)=C1

Safety Information

HS Code 

2933399990

3-chloro-4-(pyridin-2-ylmethoxy)aniline Usage And Synthesis

Uses

3-Chloro-4-(2-pyridylmethoxy)aniline was used for preparation of disubstituted (arylamino)quinolinecarbonitriles as orally active irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity and antitumor agents.

Synthesis

3-chloro-4-(pyridin-2-ylmethoxy)aniline is synthesised using 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine as a raw material by chemical reaction. The specific synthesis steps are as follows:
The 2-((2-chloro-4-nitrophenoxy)methyl)pyridine (3.9 g, 15 mmol), zinc powder (5.8 g, 88 mmol) and ammonium chloride (2.4 g, 44 mmol) were added into a mixed solution of ethanol (60 mL) and H2O (10 mL). The mixture was stirred at 60° C. overnight. Then the reaction mixture was poured into 200 mL of H2O, extracted with ethyl acetate. The organic phase was separated, washed with saturated brine and dried. The solvent was removed in vacuo, and the compound shown in the title (3.4 g, 98percent) was obtained. 1H NMR (CDCl3): δ 8.57 (1H, d, J=4.8 Hz), 7.75-7.70 (1H, m), 7.65-7.63 (1H, m), 7.23-7.20 (1H, m), 6.81 (1H, d, J=9.2 Hz), 6.77 (1H, d, J=2.8 Hz), 5.18 (2H, s), 3.48 (2H, br).

References

[1] Patent: US2016/214964, 2016, A1. Location in patent: Paragraph 0140
[2] Patent: US2006/270668, 2006, A1. Location in patent: Page/Page column 16-17
[3] Patent: US2006/270668, 2006, A1. Location in patent: Page/Page column 16-17
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 11, p. 3090 - 3104
[5] Patent: WO2009/33581, 2009, A1. Location in patent: Page/Page column 60-61

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