Dimethylformamide dimethyl acetal → HCID 18667594, compound

Temperature

150 °C

To a solution of 4-(4-methylpyridin-2-yl)-2-nitrotoluene (3.42 g) in N,N-dimethylformamide (20 ml) was added N,N-dimethylformamide dimethyl acetal (2.59 ml), and the mixture was stirred at 150° C. for 18 hours under a nitrogen atmosphere. The reaction mixture was evaporated under reduced pressure, and the residue was dissolved in tetrahydrofuran (80 ml) and water (80 ml). Sodium metaperiodate (10.59 g) was added to the solution, and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was filtered, and the filtrate was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 75 g, 0-1% ethanol in dichloromethane) to give 4-(4-methylpyridin-2-yl)-2-nitrobenzaldehyde (3.58 g).

1. customThe reaction mixture was evaporated under reduced pressure
2. dissolutionthe residue was dissolved in tetrahydrofuran (80 ml)
3. additionSodium metaperiodate (10.59 g) was added to the solution
4. stirringthe mixture was stirred at ambient temperature for 4 hours
5. filtrationThe reaction mixture was filtered
6. extractionthe filtrate was extracted with ethyl acetate
7. washThe separated organic layer was washed with brine
8. dry with materialdried over magnesium sulfate
9. customevaporated under reduced pressure
10. customThe residue was purified by column chromatography (silica gel 75 g, 0-1% ethanol in dichloromethane)

ORD record

ord-2df2cf2dd29b42b3b1bcd42ac64442b0

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06521643B1