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Chemical Structure| 2214-53-1 Chemical Structure| 2214-53-1

Structure of 2214-53-1

Chemical Structure| 2214-53-1

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Product Details of [ 2214-53-1 ]

CAS No. :2214-53-1
Formula : C7H6N2
M.W : 118.14
SMILES Code : N#CC1=CC=NC(C)=C1
MDL No. :MFCD06200207
InChI Key :SBWJLHPCEHEABR-UHFFFAOYSA-N
Pubchem ID :11959073

Safety of [ 2214-53-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331
Precautionary Statements:P261-P280-P301+P310-P311
Class:6.1
UN#:3439
Packing Group:

Application In Synthesis of [ 2214-53-1 ]

* 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.

  • Upstream synthesis route of [ 2214-53-1 ]
  • Downstream synthetic route of [ 2214-53-1 ]

[ 2214-53-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 2214-53-1 ]
  • [ 75-16-1 ]
  • [ 2732-28-7 ]
YieldReaction ConditionsOperation in experiment
25%
Stage #1: at 0℃; Heating; Reflux
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water at 20℃;
[0352] l-(2-Methyl-4-pyridinyl)ethanone (143). A solution of MeMgBr (3 M in hexanes, 6.0 mL, 17.9 mmol) was added slowly to a stirred solution of nitrile 142 (1.76 g, 14.9 mmol) in dry THF (100 mL) at 0 0C and the mixture was stirred at reflux temperature for 16 h. The mixture was cooled to 20 0C and the reaction quenched with 6 M HCl (30 mL). The aqueous fraction was separated and the organic fraction extracted with 1 M HCl (30 mL). The combined acidic fraction was stirred at 80 0C for 1 h, cooled to 0 0C and made basic with cNH3 solution. The mixture was extracted with CHCl3 (3 x 50 mL), the combined organic fraction was washed with brine (50 mL), dried and the solvent evaporated. The residue was purified by column chromatography, eluting with 50percent EtO Ac/pet, ether, to give ketone 143 (0.50 g, 25percent) as an oil: 1H NMR (CDCl3) δ 8.68 (d, J= 5.1 Hz, 1 H, H-6'), 7.59 (br s, 1 H, H-3'), 7.52 (d, J= 5.1 Hz, 1 H, H-5'), 2.65 (s, 3 H, H-2), 2.61 (s, 3 H, CH3); MS m/z 136.5 (MH+, 100percent).
References: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 787 - 797.
[2] Patent: WO2009/114552, 2009, A1, . Location in patent: Page/Page column 154.
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5028 - 5037.
  • 2
  • [ 2214-53-1 ]
  • [ 2732-28-7 ]
References: [1] Patent: US4302464, 1981, A, .
[2] Patent: WO2005/84439, 2005, A1, . Location in patent: Page/Page column 31.
 

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