3-Pyridinecarboxaldehyde → HCID 12904596, compound

To a solution of 1.88 g of 4-bromo-3-methylbenzaldehyde diethylacetal in 20 ml of diethyl ether was added dropwise 5.0 ml of a 1.4 M solution of butyllithium in hexane at -70° to 0° C., and the mixture was stirred at 0° to -50° C. for 50 minutes. To it was added dropwise 0.89 g of 3-formylpyridine at -30° to -20° C., and the reaction mixture allowed to warm to room temperature with stirring. After concentration under reduced pressure the residue was stirred with 10 ml of tetrahydrofuran and 10 ml of 2 N hydrochloric acid at room temperature for 45 minutes. The reaction mixture was basified with sodium bicarbonate, extracted with diethyl ether, and the extract was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:2) as eluent to give 1.20 g of the title compound having the following physical characteristics:

1. stirringwith stirring
2. concentrationAfter concentration under reduced pressure the residue
3. stirringwas stirred with 10 ml of tetrahydrofuran and 10 ml of 2 N hydrochloric acid at room temperature for 45 minutes
4. extractionextracted with diethyl ether
5. washthe extract was washed with a saturated aqueous solution of sodium chloride
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by column chromatography on silica gel using
9. additiona mixture of cyclohexane and ethyl acetate (1:2) as eluent

ORD record

ord-8901a083493545e19418d435349f255a

Source dataset

uspto-grants-1984_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04427682