Methyl 4-(3-methoxy-3-oxopropyl)-3-nitrobenzoate → Methyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate

The mixture of methyl 4-(3-methoxy-3-oxopropyl)-3-nitrobenzoate (12 g), THF (180 ml), and palladium-carbon (1.2 g) was stirred at room temperature for 4 days under a hydrogen atmosphere. The insolubles of the reaction mixture were separated by filtration through Celite and the filtrate was concentrated under reduced pressure. To the residue were added methanol (100 ml) and p-toluenesulfonic acid monohydrate (0.10 g), followed by heating under reflux for 1 hour, and then allowing to be cooled at room temperature. The reaction mixture was concentrated under reduced pressure. To the residue was added chloroform, followed by washing with a saturated sodium bicarbonate solution and drying over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was washed with methanol to obtain methyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate (7.0 g).

1. customThe insolubles of the reaction mixture were separated by filtration through Celite
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionTo the residue were added methanol (100 ml) and p-toluenesulfonic acid monohydrate (0.10 g)
4. temperatureby heating
5. temperatureunder reflux for 1 hour
6. temperatureto be cooled at room temperature
7. concentrationThe reaction mixture was concentrated under reduced pressure
8. additionTo the residue was added chloroform
9. washby washing with a saturated sodium bicarbonate solution
10. dry with materialdrying over anhydrous magnesium sulfate
11. customThe solvent was removed by evaporation under reduced pressure
12. washThe residue was washed with methanol

ORD record

ord-e0d633d868044a28aaef8fb11e4f44a0

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030489B2