Propanal → HCID 23510434, compound

Under nitrogen atmosphere, to a solution of methyl 2-amino-3-formylbenzoate (3.00 g) in methanol (80 ml) were added propanal (1.50 mL) and piperidine (800 μL), and the mixture was heated under reflux. To the mixture were further added propanal (700 μL) and piperidine (400 μL), and the mixture was further heated under reflux for total 4 hours. The solvent in the reaction solution was evaporated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate, and the extract was washed twice with water, and washed with a saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified twice by silica gel column (hexane/ethyl acetate=3/1→2/1→1/1) and silica gel column (hexane/ethyl acetate=3/1→2/1) to give 3-methyl-8-methoxycarbonylquinoline (2.21 g, 66%).

1. temperaturethe mixture was heated
2. temperatureunder reflux
3. temperaturethe mixture was further heated
4. temperatureunder reflux for total 4 hours
5. customThe solvent in the reaction solution was evaporated under reduced pressure, and water
6. additionwas added to the residue
7. extractionThe mixture was extracted with ethyl acetate
8. washthe extract was washed twice with water
9. washwashed with a saturated brine
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. customThe solvent was evaporated under reduced pressure
13. customthe residue was purified twice by silica gel column (hexane/ethyl acetate=3/1→2/1→1/1) and silica gel column (hexane/ethyl acetate=3/1→2/1)

ORD record

ord-d2abed9d5ace4cedb8b409ebabf2687a

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759429B2