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Chemical Structure| 379711-32-7 Chemical Structure| 379711-32-7

Structure of 379711-32-7

Chemical Structure| 379711-32-7

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Product Details of [ 379711-32-7 ]

CAS No. :379711-32-7
Formula : C20H22N2O2
M.W : 322.40
SMILES Code : O=C1C2=C(N=C(CCCC)C=C2)C3=C(C=CC(CCCC)=N3)C1=O

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Application In Synthesis of [ 379711-32-7 ]

* 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 [ 379711-32-7 ]

[ 379711-32-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 379711-32-7 ]
  • [ 613-73-0 ]
  • 3,6-di-n-butyl-naphto[2,3-f][4,5]phenanthroline-9,14-dicarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% 1 (0.98?mmol, 315?mg) and 1,2-diacetonitrilebenzene (1.13?mmol, 176?mg) were dissolved in acetonitrile (25?mL) and heated to reflux. DBU (1,8-Diazabicyclo [5.4.0] undec-7-ene, 1?mmol, 156?mg) was then added to the solution which turned dark green at once. After 4?h of reflux, the medium was let to return to room temperature and water was added. The mixture was extracted twice with dichloromethane. The organic phase was then dried on sodium sulphate, filtered and evaporated to dryness. The crude was chromatographied on silica gel (eluent: dichloromethane/triethylamine 98/2 (v/v)). The first fraction contained the desired compound and 1,2-diacetonitrilebenzene (respectively 43% and 57% molar, estimated by NMR). The latter mixture was dissolved in dichloromethane, degassed by argon bubbling, and a degassed solution of Cu(CH3CN)4PF6 (0.21?mmol, 77?mg) was syringed herein. After 30?min, the deep red solution is evaporated to dryness and subjected to chromatography column on silica gel (eluent: gradient from pure dichloromethane to a mixture of dichloromethane and methanol (98/2 v/v)). The collected orange fraction was then dissolved in acetonitrile (5?mL) and a saturated aqueous solution of KCN (5?mL) was added. The solution changes from dark red to light yellow within a few seconds. The latter was extracted twice with dichloromethane, dried on sodium sulphate, filtered and evaporated to dryness. The resulting yellow powder was the desired compound. Yield: 189?mg (44% on the overall process). 1H NMR (300?MHz, CDCl3, 25?C): delta?=?9.69 (2H, d, J?=?8.7?Hz), 8.63 (2H, dd, J?=?3.3?Hz, J?=?6.6?Hz), 7.92, (2H, dd, J?=?3.3?Hz, J?=?6.6?Hz), 7.60 (2H, d, J?=?8.7?Hz), 3.21 (4H, m), 1.94 (4H, m), 1.53 (4H, m), 1.03 (6H, t, 7.5?Hz) ppm.
 

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