2-CHLOROQUINOLINE-3-CARBALDEHYDE Chemical Properties

Melting point:

148-150 °C (lit.)

Boiling point:

335.8±22.0 °C(Predicted)

Density 

1.364

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

pka

-1.31±0.50(Predicted)

form 

Liquid

color 

Clear colorless to yellow

Sensitive 

Air Sensitive

InChIKey

SDKQWXCBSNMYBN-UHFFFAOYSA-N

CAS DataBase Reference

73568-25-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29334900

MSDS

• Language:English Provider:SigmaAldrich

2-CHLOROQUINOLINE-3-CARBALDEHYDE Usage And Synthesis

Chemical Properties

Yellow to yellow-brown crystalline powder

Synthesis

Example 7 Synthesis of 2-chloro-3-quinolinecarboxaldehyde: 1.53 mL (3.30 mmol) of n-butyllithium (n-BuLi) was added slowly and dropwise to an 8 mL THF solution containing 0.46 mL (3.30 mmol) of diisopropylamine at 0 °C. After 20 minutes of reaction, the solution was cooled to -78 °C and 2-chloroquinoline (491 mg, 3.0 mmol) was added at this temperature. The mixture was stirred at -78 °C for 30 min, followed by dropwise addition of dimethylformamide (0.39 mL, 5.04 mmol) and continued stirring at the same temperature for 30 min. Upon completion of the reaction, the reaction was quenched with glacial acetic acid (1 mL) at -78 °C, then the mixture was slowly warmed to room temperature and diluted with ether (30 mL). The organic phase was washed sequentially with saturated NaHCO3 solution (10 mL) and brine (10 mL) and dried over anhydrous MgSO4. Concentration gave 2-chloro-3-quinolinecarboxaldehyde (530 mg, 92% yield) as a light yellow solid with melting point 145-149 °C, which could be used in the next reaction without further purification. By recrystallization from ethyl acetate, a pure product was obtained as pale yellow acicular crystals with a melting point of 149-150 °C (literature values 148-149 °C, see Meth-Cohn, O.; Narhe, B.; Tarnowski, B. J. Chem. Soc. Perkin Trans. I 1981, 1520).1H NMR (300 MHz, CDCl3) δ 10.57 (s, 1H), 8.77 (s, 1H), 8.08 (d, 1H, J = 9 Hz), 8.0 (d, 1H, J = 9 Hz), 7.90 (t, 1H, J = 9 Hz), 7.67 (t, 1H, J = 9 Hz); IR (nujol) 1685, 1575, 1045, 760, 745 cm-1. 745 cm-1.

References

[1] Patent: US5212317, 1993, A
[2] Patent: US5162532, 1992, A

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