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Chemical Structure| 855765-21-8 Chemical Structure| 855765-21-8

Structure of 855765-21-8

Chemical Structure| 855765-21-8

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Product Details of [ 855765-21-8 ]

CAS No. :855765-21-8
Formula : C10H9NO3
M.W : 191.18
SMILES Code : O=C1NC2=C(C(OC)=CC=C2)C(O)=C1
MDL No. :MFCD09475798

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Application In Synthesis of [ 855765-21-8 ]

* 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 [ 855765-21-8 ]

[ 855765-21-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 141-82-2 ]
  • [ 536-90-3 ]
  • [ 27037-34-9 ]
  • [ 855765-21-8 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate; at 105℃; for 1.0h; POCl3(4.16 ml, 44.7 mmol) was added to the mixture of 3-methoxy aniline (5.0 g, 40.6 mmol) and malonic acid (4.22 g, 40.6 mmol). The reaction mass was heated to 105° C. for 1 h. The reaction mass was diluted with water (20 ml) and stirred for 30 min. The precipitated solid was filtered and washed with water. 2N NaOH solution (30 ml) was added to the solid and stirred for 18 hr. The remaining solid was filtered off and ethanol (5 ml) was added to the filtrate was acidified to PH 2 using conc. HCl. The precipitated solid was filtered and washed with water. The solid was dried under reduced pressure to get desired regio isomer in the ratio 50:50 (3 g, 38.6percent) as white solid.1H NMR (400 MHz, DMSO): delta ppm 11.27-11.07 (m, 3H), 10.01 (s, 1H), 7.68-7.65 (d, J=12 Hz, 1H), 7.41 (t, J=12 Hz, 1H) 6.91-6.88 (d, J=12 Hz, 1H), 6.76-6.72 (m, 3H), 5.62-5.60 (d, J=8 Hz, 2H), 3.92 (s, 3H), 3.72 (s, 3H).
  • 2
  • [ 27037-34-9 ]
  • [ 855765-21-8 ]
  • [ 55934-21-9 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
39% In ethyl acetate; trichlorophosphate; Step 2: Preparation of 2,4-dichloro-5-methoxyquinoline and 2,4-dichloro-7-methoxyquinoline A solution of 4-hydroxy-5-methoxyquinoline-2(1H)-one and <strong>[27037-34-9]4-hydroxy-7-methoxyquinoline-2(1H)-one</strong> (3 g, 15.70 mmol) in POCl3 (3.66 ml, 39.2 mmol) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20percent ethyl acetate in pet ether) to afford mixture of regioisomers. This mixture of regioisomers was separated by SFC purification to afford 2,4-dichloro-5-methoxyquinoline (0.7 g, 39percent) and 2,4-dichloro-7-methoxyquinoline (required isomer) (1.3 g, 72.6percent) as white solid. 2,4-dichloro-7-methoxyquinoline: 1H NMR (400 MHz, CDCl3): delta ppm 8.07-8.04 (d, J=12 Hz, 1H), 7.35-7.34 (m, 2H), 7.28-7.26 (m, 1H), 3.94 (s, 3H);
  • 3
  • [ 27037-34-9 ]
  • [ 855765-21-8 ]
  • [ 55934-21-9 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; trichlorophosphate; Step 2: Preparation of 2,4-dichloro-5-methoxyquinoline and 2,4-dichloro-7-methoxyquinoline A solution of 4-hydroxy-5-methoxyquinoline-2(1H)-one and <strong>[27037-34-9]4-hydroxy-7-methoxyquinoline-2(1H)-one</strong> (3 g, 15.70 mmol) in POCl3 (3.66 m, 39.2 mmol) was refluxed for 3 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20percent ethyl acetate in pet ether) to get regio isomers as mixture was separated by SFC purification to get desired compound 2,4-dichloro-5-methoxyquinoline (0.7 g, 39percent) and 2,4-dichloro-7-methoxyquinoline (required isomer) (1.3 g, 72.6percent) as white solid.
 

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