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Chemical Structure| 55934-22-0 Chemical Structure| 55934-22-0

Structure of 55934-22-0

Chemical Structure| 55934-22-0

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Product Details of [ 55934-22-0 ]

CAS No. :55934-22-0
Formula : C10H7Cl2NO
M.W : 228.07
SMILES Code : COC1=CC=C2C(Cl)=CC(Cl)=NC2=C1
MDL No. :MFCD09475797
InChI Key :XHKVDLMHZLUDSK-UHFFFAOYSA-N
Pubchem ID :22832054

Safety of [ 55934-22-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 55934-22-0 ]

* 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 [ 55934-22-0 ]

[ 55934-22-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 27037-34-9 ]
  • [ 55934-22-0 ]
YieldReaction ConditionsOperation in experiment
60 - 82% A suspension of 4-hydroxy-7-methoxy-2-oxo-l,2-dihydroquinoline (Faber K. etal, J. Heterocyclic chem., 1985 22, 1080) (5.0 g, 26.17 mmol) in POCl3 (25 mL, 261.7 mmol) was heated at 115 0C for 3 h (clear solution obtained upon heating). After 3 h, the reaction mixture was concentrated under reduced pressure. The residue was poured into iced water (40 mL), pH was then adjusted to 10 with 3N NaOH and extracted with CHCl3 (3 x 100 mL). The combined CHCl3 layers were washed with brine and dried (MgSO4). The organic layer EPO <DP n="73"/>was then filtered and concentrated to give 2,4-Dichloro-7-methoxy-quinoline (4.9 g, 21.49 mmol, 82percent yield) as brown solid. MS m/z 229 (M++..).
  • 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);
 

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