Biphenyl → HCID 67304705, compound

HRID 1009743Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([NH:7][CH:8]=[C:9]2[C:14](=[O:15])OC(C)(C)OC2=O)=[CH:5][C:4]=1[C:21]([O:23][CH3:24])=[O:22].C1(C2C=CC=CC=2)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[CH3:1][O:2][C:3]1[CH:20]=[C:19]2[C:6](=[CH:5][C:4]=1[C:21]([O:23][CH3:24])=[O:22])[NH:7][CH:8]=[CH:9][C:14]2=[O:15]

Participants

Conditions

Temperature: 260 °C

Procedure

5-(4-Methoxy-3-methoxycarbonylanilinomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (28.9 g) was added portionwise to a mixture (200 ml) of biphenyl and diphenyl ether (‘Dowtherm A’) that had been warmed to 260° C. The solution was stirred at that temperature for 5 minutes. The resultant mixture was cooled to ambient temperature and added to a mixture of petroleum ether (250 ml) and diethyl ether (250 ml). The precipitate was collected by filtration and washed with petroleum ether. The material so obtained was purified by column chromatography on silica using increasingly polar solvent mixtures of methylene chloride and methanol (from 10:0 to 17:3) as eluent. There was thus obtained a 7:3 mixture (11.7 g) of 6-methoxy-7-methoxycarbonyl-1,4-dihydroquinolin-4-one and 6-methoxy-5-methoxycarbonyl-1,4-dihydroquinolin-4-one; 1H NMR: (DMSOd6) 3.85 (s, 3H), 3.88 (s, 3H), 6.05 (d, 1H), 7.61 (s, 1H), 7.87 (s, 1H), 7.94 (d, 1H) and 3.75 (s, 3H), 3.82 (s, 3H), 5.92 (d, 1H), 7.55 (d, 1H), 7.63 (d, 1H), 7.88 (m, 1H); Mass Spectrum: M+H+ 234.

Workup

filtrationThe precipitate was collected by filtration
washwashed with petroleum ether
customThe material so obtained
customwas purified by column chromatography on silica using
temperatureincreasingly polar solvent mixtures of methylene chloride and methanol (from 10:0 to 17:3) as eluent

Sources & evidence

ORD record: ord-9af9df04508d4eb7b07a1498148fb42d
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973164B2

Reaction notes

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