Diethyl Malonate → 1,2-Dihydro-2-oxo-4-(2-pyridyl)-3-quinolinecarboxylic acid

HRID 1081329Notes

Reaction equation

[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=O.[C:16](OCC)(=[O:23])[CH2:17][C:18]([O:20]CC)=[O:19]>>[O:23]=[C:16]1[C:17]([C:18]([OH:20])=[O:19])=[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[C:3]2[C:2](=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:1]1

Participants

Reactant 2

HCID 7761Diethyl Malonate

HCID 27565322-(2-Aminobenzoyl)pyridine

Product 1

HCID 233640641,2-Dihydro-2-oxo-4-(2-pyridyl)-3-quinolinecarboxylic acid

Conditions

Temperature: 180 °C

Procedure

A mixture of 2-(2-aminobenzoyl)pyridine (4.36 g), diethyl malonate (3.92 ml) and 1,9-diazabicyclo[5.4.0]-7-undecene(0.5 ml) was heated for 3 hours at 180° C. The reaction mixture was cooled to give ethyl ester of 1,2-dihydro-2-oxo-4-(2-pyridyl)-3-quinolinecarboxylic acid as crystals (6.1 g: unrefined). The crystalline product was dissolved in DMF (100 ml), to which sodium hydride (60% oily) (1.5 g) was added, and the mixture was stirred for one hour at room temperature. The mixture was cooled to 0° C., to which was added, while stirring, iodomethane (10 ml). The mixture was stirred for one hour at room temperature, which was then concentrated. To the concentrate was added ethyl acetate. The mixture was washed with water and dried. The solvent was then distilled off. The residue was purified by means of a silica-gel column chromatography (ethyl acetate) to give ethyl eater of 1,2-dihydro-1-methyl-2-oxo-4-(2-pyridyl)-3-quinoline carboxylic acid as pale yellow crystals (2.6 g).

Workup

temperatureThe reaction mixture was cooled

Sources & evidence

ORD record: ord-6c65b05c3fec45f681477a82d9c3ee81
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05585385

Reaction notes

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