Hydrochloric Acid → N-(3-formylpyridin-4-yl)-2,2-dimethylpropanamide

Temperature

-78 °C

2,2-Dimethyl-N-pyridin-4-yl-propionamide (5.60 g) was dissolved in tetrahydrofuran (70 ml) to prepare a solution which was then cooled to −78° C. A 1.57 M n-butyllithium/n-hexane solution (62 ml) was gradually added dropwise thereto, and the mixture was stirred at −78° C. for 15 min. The reaction solution was stirred at 0° C. for 4 hr and was then again cooled to −78° C. A solution of N,N-dimethylformamide (6.69 g) in tetrahydrofuran (7 ml) was gradually added dropwise thereto. The temperature of the reaction solution was raised to room temperature, the reaction solution was then poured into a mixture composed of ice (10 g) and 6 N hydrochloric acid (30 ml), and the mixture was stirred at room temperature for 15 min. The aqueous layer was neutralized with potassium carbonate powder and was extracted with diethyl ether. The diethyl ether layer was then washed with water and saturated brine and was dried over magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give N-(3-formyl-pyridin-4-yl)-2,2-dimethyl-propionamide (3.35 g, yield 52%).

1. customto prepare a solution which
2. stirringThe reaction solution was stirred at 0° C. for 4 hr
3. temperaturewas then again cooled to −78° C
4. temperatureThe temperature of the reaction solution was raised to room temperature
5. additionthe reaction solution was then poured into a mixture
6. stirringthe mixture was stirred at room temperature for 15 min
7. extractionwas extracted with diethyl ether
8. washThe diethyl ether layer was then washed with water and saturated brine
9. dry with materialwas dried over magnesium sulfate
10. customThe solvent was removed by distillation under the reduced pressure
11. customthe residue was purified by column chromatography

ORD record

ord-1ee9b5383f834ff6b78074f9d893f050

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560558B2