Sodium Chloride → 6-Chloropyridine-3-carbaldehyde

Temperature

-20 °C

In tetrahydrofuran (8 ml), 6-chloro-N-methoxy-N-methylnicotinamide (500 mg) was dissolved, followed by the dropwise addition of diisobutylaluminum hydride (a 0.95M hexane solution, 2.88 ml) at −78° C. in an argon gas atmosphere. The resulting mixture was stirred for 3 hours and then, at room temperature, for 2 hours. After the reaction mixture was cooled to −20° C., saturated aqueous NaCl solution (2 ml) was added thereto, followed by stirring for 30 minutes. The insoluble matter was filtered off. The residue was washed with ethyl acetate. The filtrate and the washing were combined together. The mixture was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure, whereby the title compound (346 mg, 98%) was obtained as a crude product. The product was provided for the subsequent reaction without purification.

1. waitat room temperature, for 2 hours
2. stirringby stirring for 30 minutes
3. filtrationThe insoluble matter was filtered off
4. washThe residue was washed with ethyl acetate
5. washThe mixture was washed with saturated aqueous NaCl solution
6. dry with materialdried over anhydrous sodium sulfate
7. distillationThe solvent was then distilled off under reduced pressure, whereby the title compound (346 mg, 98%)

ORD record

ord-43b93937b07b4eb8b745ba5ddc772851

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06747023B1