2-CHLORO-6-NITROQUINOLINE Chemical Properties

Melting point:

236-237 ºC

Boiling point:

363.4±22.0 °C(Predicted)

Density 

1.484

storage temp. 

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

pka

-1.42±0.43(Predicted)

form 

solid

color 

Grey

Safety Information

HS Code 

2933499090

2-CHLORO-6-NITROQUINOLINE Usage And Synthesis

Synthesis Reference(s)

The Journal of Organic Chemistry, 67, p. 7884, 2002 DOI: 10.1021/jo016196i

Synthesis

Step 4 Synthesis of 2-chloro-6-nitroquinoline: To a solution of 6-nitro-3,4-dihydroquinolin-2(1H)-one (8.2 g, 41.9 mmol) in benzene (150 mL) was added DDQ (9.6 g, 42.5 mmol) and phosphorus triclosan (20.5 mL) sequentially, and the homogeneity of the reaction system was maintained during dropwise addition. The reaction mixture was heated to 90 °C with continuous stirring for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was subsequently quenched by slowly pouring into 500 mL of ice water. The pH was adjusted to 7 with 4N NaOH solution. extraction was carried out with ethyl acetate (3 x 1 L) and the organic phases were combined. The organic phase was concentrated under reduced pressure to give 8.4 g of 2-chloro-6-nitroquinoline in yellow solid form in 95% yield.

References

[1] Heterocycles, 1998, vol. 48, # 12, p. 2637 - 2641
[2] Patent: US2007/27184, 2007, A1. Location in patent: Page/Page column 18; 25
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 20, p. 5270 - 5274
[4] Patent: KR101576386, 2015, B1. Location in patent: Paragraph 0190; 0193-0194

2-CHLORO-6-NITROQUINOLINE(29969-57-1)Related Product Information

• 4-Chloro-3-nitroquinoline
• 6-NITROQUINOLINE