Br 8 NH₂ 9 HC(OME)3 reflux T=" Ph₂O reflux H Br 10 Br 11 2,2-Dimethyl-5-(4-bromophenylaminomethylene)-1,3-dioxan-4,6-dione (10): Dissolve Meldrum's acid (9, pKa = 4.97) (4.60 g, 31.9 mmol) in methyl orthoformate (60 mL) and then heat to reflux for 2 h under a nitrogen atmosphere (use a balloon). Cool the reaction mixture to room temperature then add 4-bromoaniline (3.80 g, 22.1 mmol) and heat to reflux for 6 h.5 Allow to cool to room temperature and collect the precipitated solid and recrystallize from methanol. Obtain a melting point for the resulting purified solid. 6-Bromo-4-oxo-4H-quinoline (11): Dissolve 10 (2.00 g, 6.12 mmol) in hot6 diphenyl ether (31 mL) and then heat to reflux until the formation of gaseous products ceases. After cooling to room temperature, add an equal volume of petroleum ether (bp 40- 60 °C) and allow to stand for 48 h. Isolate the product by filtration and wash with petroleum ether.7 Use deuterated DMSO as the solvent when preparing an NMR sample of this compound.

Br 8 NH₂ 9 HC(OME)3 reflux T=" Ph₂O reflux H Br 10 Br 11 2,2-Dimethyl-5-(4-bromophenylaminomethylene)-1,3-dioxan-4,6-dione (10): Dissolve Meldrum's acid (9, pKa = 4.97) (4.60 g, 31.9 mmol) in methyl orthoformate (60 mL) and then heat to reflux for 2 h under a nitrogen atmosphere (use a balloon). Cool the reaction mixture to room temperature then add 4-bromoaniline (3.80 g, 22.1 mmol) and heat to reflux for 6 h.5 Allow to cool to room temperature and collect the precipitated solid and recrystallize from methanol. Obtain a melting point for the resulting purified solid. 6-Bromo-4-oxo-4H-quinoline (11): Dissolve 10 (2.00 g, 6.12 mmol) in hot6 diphenyl ether (31 mL) and then heat to reflux until the formation of gaseous products ceases. After cooling to room temperature, add an equal volume of petroleum ether (bp 40- 60 °C) and allow to stand for 48 h. Isolate the product by filtration and wash with petroleum ether.7 Use deuterated DMSO as the solvent when preparing an NMR sample of this compound.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.SE: Something Extra

Problem 62GP: The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a...

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