1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Ethyl 4-hydroxy-7,8-dimethoxyquinoline-3-carboxylate

HRID 525948Notes

Reaction equation

C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[CH3:26][O:27][C:28]1[C:33]([O:34][CH3:35])=[CH:32][CH:31]=[CH:30][C:29]=1[NH:36][CH:37]=[C:38]([C:44]([O:46]CC)=O)[C:39]([O:41][CH2:42][CH3:43])=[O:40]>CCCCCC>[CH3:35][O:34][C:33]1[C:28]([O:27][CH3:26])=[C:29]2[C:30]([C:44](=[O:46])[C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][NH:36]2)=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 250 °C

Procedure

To Dowtherm A (100 mL) heated at 250° C. was added diethyl 2-(((2,3-dimethoxyphenyl)amino)methylene)malonate (48 g, 148 mmol). The mixture was stirred at 250° C. for 1 h. LCMS indicated completion of the reaction. The reaction mixture was allowed to cool a bit and was then added to cold hexane, the precipitates were collected by filtration, washed with hexane and then allowed to dry in the air to afford ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (35 g, 126 mmol, 85% yield) as brown solid. LCMS: (M+H)+: 278.2.

Workup

customcompletion of the reaction
temperatureto cool a bit
filtrationthe precipitates were collected by filtration
washwashed with hexane
customto dry in the air

Sources & evidence

ORD record: ord-7d67748b45ba47b0ac124eab6bb9d61e
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340556B2

Reaction notes

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