4-Pyridinecarboxaldehyde → HCID 11694508, compound

Temperature

30 °C

Under a dry nitrogen atmosphere, an appropriate amount of freshly cut magnesium chips was suspended in 150 mL of THF. To this was added about 5% of a solution of 22.5 grams (0.100 mole) of 4-bromobenzotrifluoride in 75 mL of THF. The reaction mixture was then warmed to about 30° C. to initiate the reaction. Once the reaction was proceeding, the remainder of the solution of 4-bromobenzotrifluoride was added during a one hour period, at a rate to maintain the reaction mixture temperature at about 34° C. to about 38° C. Upon completion of addition, the reaction mixture was stirred during a one hour period, as it cooled to ambient temperature. After this time a solution of 8.5 grams (0.075 mole) of 4-pyridinecarboxaldehyde in 75 mL of THF was added portion wise while maintaining the reaction mixture temperature below 30° C. Upon completion of addition the reaction mixture was stirred at ambient temperature for about 18 hours. With vigorous stirring the reaction mixture was then poured into 600 mL of aqueous 10% ammonium chloride. The mixture was extracted with two 300 mL portions of ethyl acetate. The combined extracts were washed with 250 mL of an aqueous solution saturated with sodium chloride, then dried with magnesium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure, yielding 21.2 grams of the subject compound. The product was used without purification in the following reaction.

1. customthe reaction
2. temperatureto maintain the reaction mixture temperature at about 34° C. to about 38° C
3. additionUpon completion of addition
4. temperaturecooled to ambient temperature
5. temperaturewhile maintaining the reaction mixture temperature below 30° C
6. additionUpon completion of addition the reaction mixture
7. stirringwas stirred at ambient temperature for about 18 hours
8. stirringWith vigorous stirring the reaction mixture
9. extractionThe mixture was extracted with two 300 mL portions of ethyl acetate
10. washThe combined extracts were washed with 250 mL of an aqueous solution saturated with sodium chloride
11. dry with materialdried with magnesium sulfate
12. filtrationThe mixture was filtered
13. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-dca0c57d39df4ded8840414d0f511b57

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683070B2