m-Toluidine → Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 48278

Reaction equation

C(O[CH2:4][CH:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:13][C:11]1[C:22]2[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=2)[N:16]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

Diethyl ethoxymethylmalonate (37.8 mL, 187 mmol) and m-toluidine (20.0 mL, 187 mmol) were combined and heated at 100° C. for about 3 hours. The reaction mixture was allowed to cool to ambient temperature and it solidified. Dowtherm A (350 mL) was added and the reaction mixture was heated at reflux for about 30 minutes. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration, rinsed with acetone and dried to provide 33 g of ethyl 4-hydroxy-7-methyl-3-quinolinecarboxylate as a tan powder.

Workup

temperatureto cool to ambient temperature
temperaturethe reaction mixture was heated
temperatureat reflux for about 30 minutes
temperatureto cool to ambient temperature
customThe resulting precipitate was isolated by filtration
washrinsed with acetone
customdried

Sources & evidence

ORD record: ord-6cf1c116571243d7825cd4a86ae22e11
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703402B2

Linked notes

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