ChemicalBook CAS DataBase List 2-CHLOROQUINOLINE-3-CARBALDEHYDE

2-CHLOROQUINOLINE-3-CARBALDEHYDE synthesis

5synthesis methods

Product Name:2-CHLOROQUINOLINE-3-CARBALDEHYDE
CAS Number:73568-25-9
Molecular formula:C10H6ClNO
Molecular Weight:191.61

612-62-4 Synthesis

612-62-4
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73568-25-9
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$9.00/250mg

Yield:73568-25-9 92%

Reaction Conditions:

with n-butyllithium;diisopropylamine in tetrahydrofuran;N-methyl-acetamide;acetic acid

Steps:

7 2-Chloro-3-quinolinecarboxaldehyde
EXAMPLE 7 2-Chloro-3-quinolinecarboxaldehyde To a solution of 0.46 mL (3.30 mmol) of diisopropylamine in 8 mL of THF at 0° C. was added 1.53 mL (3.30 mmol) of n-BuLi dropwise. After 20 min the solution was cooled to -78° C. and 2-chloroquinoline (491 mg, 3.0 mmol) was added neat. The mixture was stirred at -78° C. for 30 min, then dimethylformamide (0.39 mL, 5.04 mmol) was added dropwise and the reaction mixture was stirred an additional 30 min at this temperature. After quenching at -78° C. with glacial acetic acid (1 mL), the mixture was warmed to room temperature and diluted with ether (30 mL). The organic phase was washed with saturated NaHCO₃ solution (10 mL) and brine (10 mL), and was dried over MgSO₄. Concentration afforded 2-chloro-3-quinolinecarboxaldehyde (530 mg, 92%) as a light yellow solid (mp 145°-149 ° C.), which was used directly in the next step without further purification. Recrystallization from ethyl acetate afforded the pure compound as light yellow needles: mp 149°-150° C. (mp 148°-149° C. reported in Meth-Cohn, O.; Narhe, B.; Tarnowski, B. J. Chem. Soc. Perkin Trans. I 1981, 1520.). ¹ H 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.

References:

North Carolina State University US5212317, 1993, A

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