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Chemical Structure| 925890-60-4 Chemical Structure| 925890-60-4

Structure of 925890-60-4

Chemical Structure| 925890-60-4

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Product Details of [ 925890-60-4 ]

CAS No. :925890-60-4
Formula : C10H8INO
M.W : 285.08
SMILES Code : COC1=CC=C2C(I)=CC=NC2=C1

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Application In Synthesis of [ 925890-60-4 ]

* 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 [ 925890-60-4 ]

[ 925890-60-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 68500-37-8 ]
  • [ 925890-60-4 ]
YieldReaction ConditionsOperation in experiment
Example 70; 4-Benzyl-3-(2-(7-methoxyqumolm-4-yloxy)ethyl)pyridin-2(l//)-one <n="116"/>4-Iodo-7-methoxyquinoline: The general procedure is described in Drake, N. L.; Creech, H. J.; Garman, J. A.; Haywood, S. T.; Peck, R. M.; Van Hook, J. O.; Walton, E., Synthetic antimalarials. The preparation of certain 4- aminoquinolines. Journal of the American Chemical Society 1946, 68, 1208-13. A dry 250 mL, 1-neck round bottomed flask was charged with 4-chloro-7- methoxyquinoline (1.77 g, 9.1 mmol), and 100 mL dry dioxane. The solution was treated with 20 mL IN HCl in Et2O. The solution was occasionally swirled over a 15 minute period, and the solvent was removed in vacuo. The residue was dried at 60 °C at 0.1 mmHg for 2 h. To the flask was added a stir bar and 20 mL dry acetonitrile. The flask was fitted with a reflux condenser, and to the stirring slurry was added sodium iodide (4.1 g, 27 mmol). The solution was heated to reflux for 48 h. The solution was cooled, and the solution was filtered. The precipitate was washed with ACN (3 x 20 mL), and water (3 x 20 mL). The solid was suspended in 70percent CH2C12-3Opercent MeOH. To the solution was added Si-carbonate (16 g, 11 mmol). The slurry was swirled for 1 h, and filtered. The silica was washed with EtOH (3x 50 mL). The solvent was removed in vacuo to afford 4-iodo-7- methoxyquinoline. 1H NMR (300 MHz, MeOD) delta ppm 4.00 (s, 3 H) 7.35 (dd, <n="117"/>J=I 0.01, 2.48 Hz, 1 H) 7.36 (d, J=2.56 Hz, 1 H) 8.00 (d, J=9.87 Hz, 1 H) 8.01 (d, J=4.75 Hz, 1 H) 8.33 (d, J=4.90 Hz, 1 H). 13C NMR (101 MHz, MeOD) delta ppm 56.46 (s, 1 C) 107.73 (s, 1 C) 113.18 (s, 1 C) 122.61 (s, 1 C) 127.31 (s, 1 C) 132.05 (s, 1 C) 134.27 (s, 1 C) 150.18 (s, 1 C) 150.86 (s, 1 C) 163.35 (s, 1 C). MS (ESI pos. ion) m/z (MH+): 286.0, calcd for Ci0H8INO + H+ = 286.0.
 

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