2,4-DICHLORO-3-NITRO-QUINOLINE Chemical Properties

Melting point:

102 °C(Solv: methanol (67-56-1); ethyl acetate (141-78-6))

Boiling point:

359.7±37.0 °C(Predicted)

Density 

1.593±0.06 g/cm3(Predicted)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

-4.98±0.50(Predicted)

color 

White to Off-White

InChI

InChI=1S/C9H4Cl2N2O2/c10-7-5-3-1-2-4-6(5)12-9(11)8(7)13(14)15/h1-4H

InChIKey

RSFJVCHKGRUCIC-UHFFFAOYSA-N

SMILES

N1C2C(=CC=CC=2)C(Cl)=C([N+]([O-])=O)C=1Cl

Safety Information

HS Code 

2933499090

2,4-DICHLORO-3-NITRO-QUINOLINE Usage And Synthesis

Uses

2,4-Dichloro-3-nitroquinoline has antitumor activity.

Uses

2,4-Dichloro-3-nitroquinoline has antitumor activity.

Synthesis

(2) Synthesis of 2,4-dichloro-3-nitroquinoline: In a 20 mL round-bottomed flask, 3-nitroquinoline-2,4-diol (1 g, 4.85 mmol), phosphorus trichloride (appropriate amount) and N,N-dimethylaniline (0.19 mL) were added sequentially. The reaction mixture was stirred at 90 °C for 2 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature, slowly poured into ice water, and stirring was continued for 0.5 hours. The precipitate precipitated was collected by filtration and dried under vacuum overnight. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=5:1, v/v) to give 0.7 g of white solid product in 59.4% yield.

References

[1] Medicinal Chemistry Research, 2014, vol. 23, # 6, p. 2964 - 2975
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 11, p. 4450 - 4465
[3] Patent: WO2013/67597, 2013, A1. Location in patent: Page/Page column 78
[4] Patent: WO2018/191746, 2018, A1. Location in patent: Paragraph 0391
[5] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 921 - 926

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