Ammonia → 3-Pyridinecarbonitrile, 5-formyl-6-methoxy-

Temperatur

100 °C

2.00 g of 5-bromo-2-methoxy-3-pyridinecarboxaldehyde dimethyl acetal was dissolved in 25 ml of propionitrile. To the mixture were added 449 mg of sodium cyanide, 152 mg of cuprous iodide and 462 mg of tetrakis(triphenylphosphine)palladium, followed by stirring at 100° C. for 45 minutes in nitrogen atmosphere. A diluted ammonia was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, to give an oil. The oil was dissolved in 16 ml of acetone, 4 ml of 5N-hydrochloric acid was added thereto, and the mixture was left for 30 minutes at room temperature. An aqueous sodium carbonate aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (toluene:ethyl acetate=1:1), to give 843 mg of the title compound as white crystals.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed with water and brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was evaporated
5. customto give an oil
6. waitthe mixture was left for 30 minutes at room temperature
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with water and brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was evaporated
11. customthe crude product was purified by silica gel column chromatography (toluene:ethyl acetate=1:1)

ORD-Eintrag

ord-8971683554db45fd958b06e1be245f9c

Quelldatensatz

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06784192B2