ChemicalBook CAS DataBase List 3-Quinolinecarbonitrile, 7-broMo-4-hydroxy-

3-Quinolinecarbonitrile, 7-broMo-4-hydroxy- synthesis

4synthesis methods

Product Name:3-Quinolinecarbonitrile, 7-broMo-4-hydroxy-
CAS Number:958648-90-3
Molecular formula:C10H5BrN2O
Molecular Weight:249.06

94-05-3 Synthesis

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3-Quinolinecarbonitrile, 7-broMo-4-hydroxy-

958648-90-3
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Yield:-

Reaction Conditions:

with biphenyl in N-methyl-acetamide;diphenylether;toluene;

Steps:

R.4 7-Bromo-4-oxo-1,4-dihydroquinoline-3-carbonitrile

REFERENCE EXAMPLE 4 7-Bromo-4-oxo-1,4-dihydroquinoline-3-carbonitrile A mixture of ethyl(ethoxymethylene) cyanoacetate (30 g, 180 mmol) and 3-bromoaniline (25.0 g, 145 mnol) in 300 mL of toluene was heated at reflux for 7 hours. Upon cooling to room temperature a white solid formed. The solid was collected by filtration washing with toluene. -The olefin (30.0 g, 101 mmol) was dissolved in 600 mL of a 3 to 1 mixture of diphenyl ether and biphenyl and the solution was heated at 259-260° C. (internal temperature) with the ethanol formed in the reaction removed by distillation. After heating overnight, the solution was cooled to room temperature and poured into hexane. The precipitate was collected to provide 22.0 g of a solid that was combined with 275 mL of dimethylformamide, heated at 100° C. and then filtered to provide 9.0 g (36% yield) of 7-bromo-4-oxo-1,4-dihydroquinoline-3-carbonitrile; H NMR (DMSO- d₆) δ-7.64 (dd, J =9, 2 Hz, 1H), 7.82 (d, J =2 Hz, 1H), 8.04 (d, J=9 Hz, 1H), 8.78 (s, 1H); MS (ES) m/z 248.8 (M +1)-1H-. Analysis for C₁₀H₅ BrN₂O: Calcd: C, 48.22;H, 2.02; N, 11.25.Found: C, 48.31;H, 1.93; N, 11.33.

References:

US2002/26052,2002,A1

20776-50-5 Synthesis