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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.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Please help me calculate the theoretical yield(s) for this reaction as seen in the photo! All necessary information can be found there.
Br 8 NH₂ 9 HC(OME) 3 reflux Br. H 10 Ph₂O reflux Br. 11 H 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 hot 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.
Transcribed Image Text:Br 8 NH₂ 9 HC(OME) 3 reflux Br. H 10 Ph₂O reflux Br. 11 H 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 hot 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.
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