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Chemical Structure| 868395-55-5 Chemical Structure| 868395-55-5

Structure of 868395-55-5

Chemical Structure| 868395-55-5

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Product Details of [ 868395-55-5 ]

CAS No. :868395-55-5
Formula : C9H8N2O
M.W : 160.17
SMILES Code : N#CCC(C1=NC=C(C)C=C1)=O
MDL No. :MFCD11519235

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Application In Synthesis of [ 868395-55-5 ]

* 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 [ 868395-55-5 ]

[ 868395-55-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 55876-82-9 ]
  • [ 75-05-8 ]
  • [ 868395-55-5 ]
YieldReaction ConditionsOperation in experiment
84% With sodium ethanolate; In toluene; for 5h;Reflux; EXAMPLE 2 Synthesis of (5-amino-1H-pyrazol-4-yl)-(5-methylpyridin-2-yl)-methanone Sodium (2.2 g, 0.0963 moles) and anhydrous ethanol were combined and stirred until dissolved. The ethanol and azeotrope were stripped off with anhydrous toluene (35 ml). Additional anhydrous toluene (35 ml) was added followed by <strong>[55876-82-9]ethyl-5-methylpyridinecarboxylate</strong> (15.9 g, 0.0963 moles) and anhydrous acetonitrile (6.6 ml, 0.125 moles). The mixture was refluxed for 5 hrs then stirred at room temperature overnight. The reaction was then diluted with heptane (300 ml) and the solid was filtered and dried. LC/MS M +H 161. The solid was then suspended in dichloromethane (150 ml) and acidified with acetic acid. The mixture was filtered through a silica gel plug with dichloromethane. The organic portions were removed to yield a dark brown solid, 3-(5-methylpyridin-2-yl)-3-oxopropionitrile (12.98 g, 84% yield), which was used without further purification. Next, 3-(5-methylpyridin-2-yl)-3-oxopropionitrile (12.98 g, 0.081 moles) and dichloromethane (150 ml) were combined and cooled to -10 C. Dimethylformamide dimethylacetal (2.57 g, 0.0216 moles) was added. TLC showed the reaction was complete after 2 hours. The reaction was concentrated to a brown oil. LC/MS M +H 216. Next, the brown oil was dissolved in ethanol (125 ml) with aminoguanidine nitrate (14.1 g, 0.103 moles) and 10 N sodium hydroxide (8.5 ml). After 5 hours at reflux the reaction was cooled to room temperature and stirred overnight. LC/MS showed that the reaction was complete. The solvent was stripped off and the residue dissolved in ethyl acetate and washed with water (2 X), dried over magnesium sulfate, filtered and stripped to a brown solid which was identified as (3-amino-1H-pyrazol-4-yl)-(5-methylpyridin-2-yl)-methanone (5.27 g, 32% yield). LC/MS M +H 203. 1H NMR (DMSO) 2.39 (3H, s, CH3), 6.88 (2H, br, s), 7.8 (1H, d), 7.9 (1H, d), 8.32 (1H, s), 856 (1H, s), 11.88 (1H, br, s).
 

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