Hexane → 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 saline (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 saline 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. additionsaturated saline (2 ml) was added
3. stirringby stirring for 30 minutes
4. filtrationThe insoluble matter was filtered off
5. washThe residue was washed with ethyl acetate
6. washThe mixture was washed with saturated saline
7. dry with materialdried over anhydrous sodium sulfate
8. distillationThe solvent was then distilled off under reduced pressure, whereby the title compound (346 mg, 98%)

ORD record

ord-b0f0d9881c27421f81f806ccea56a338

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06525042B1