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Chemical Structure| 666735-00-8 Chemical Structure| 666735-00-8

Structure of 666735-00-8

Chemical Structure| 666735-00-8

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Product Details of [ 666735-00-8 ]

CAS No. :666735-00-8
Formula : C11H11NO2
M.W : 189.21
SMILES Code : O=C1C=CNC2=C1C=C(OC)C(C)=C2

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Application In Synthesis of [ 666735-00-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 666735-00-8 ]

[ 666735-00-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 15568-85-1 ]
  • [ 3913-23-3 ]
  • [ 666735-00-8 ]
YieldReaction ConditionsOperation in experiment
23% 2-Bromomethyl-1-methoxy-4-nitrobenzene (2.03 g) was dissolved in N,N-dimethylformamide (30 ml). Triethylamine (5 ml) and 20% palladium hydroxide (1.08 g) were added to the solution, and the mixture was stirred under a hydrogen gas atmosphere at room temperature overnight. The reaction mixture was filtered and was then washed with chloroform. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue as such was used in the next reaction without purification. The residue and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (2.00 g) were suspended in 2-propanol (40 ml), and the suspension was stirred at 70C for 30 min. The reaction mixture was cooled to room temperature, and the precipitated crystal was then collected by filtration and was washed with methanol and then with ether. The crystal thus obtained as such was used in the next reaction without further purification. The crystal prepared above and biphenyl (5.9 g) were suspended in diphenyl ether (15 ml), and the suspension was stirred at 220C for 3 hr. The reaction mixture was cooled to room temperature, and the cooled reaction mixture as such was purified by column chromatography with an ethyl acetate-hexane system to give 6-methoxy-7-methyl-1H-quinolin-4-one (352 mg, yield 23%) (3 steps).
 

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