Dimethyl (4-methoxy-2-nitrobenzyl)malonate → 7-Methoxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylic acid

HRID 382962Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][CH:8]([C:13]([O:15]C)=[O:14])[C:9](OC)=[O:10])=[C:5]([N+:19]([O-])=O)[CH:4]=1.[H][H]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH2:7][CH:8]([C:13]([OH:15])=[O:14])[C:9](=[O:10])[NH:19]2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of dimethyl (4-methoxy-2-nitrobenzyl)malonate (19 g) in ethanol (200 ml) was hydrogenated in the presence of 10% palladium-C (2.0 g) at room temperature under one atmosphere of hydrogen for 24 hr. The reaction mixture was further stirred at 80° C. for 24 hr and the catalyst was removed by filtration. The filtrate was concentrated. The residue was dissolved in the combined solvent of THF (250 ml) and methanol (250 ml) and 1 N aqueous sodium hydroxide (126 ml) was added in an ice bath. The reaction mixture was stirred at room temperature for 72 hr and concentrated. The residue was made acidic by adding 1 N aqueous hydrochloric acid and the precipitate was collected by filtration. The crude crystals were washed with acetone to obtain the titled compound (11.7 g).

Workup

customthe catalyst was removed by filtration
concentrationThe filtrate was concentrated
dissolutionThe residue was dissolved in the combined solvent of THF (250 ml) and methanol (250 ml) and 1 N aqueous sodium hydroxide (126 ml)
additionwas added in an ice bath
stirringThe reaction mixture was stirred at room temperature for 72 hr
concentrationconcentrated
additionby adding 1 N aqueous hydrochloric acid
filtrationthe precipitate was collected by filtration
washThe crude crystals were washed with acetone

Sources & evidence

ORD record: ord-cdd9638919084b7ca3c897f47184249a
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310107B1

Reaction notes

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