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Chemical Structure| 884495-36-7 Chemical Structure| 884495-36-7

Structure of 884495-36-7

Chemical Structure| 884495-36-7

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Product Details of [ 884495-36-7 ]

CAS No. :884495-36-7
Formula : C7H6ClNO
M.W : 155.58
SMILES Code : O=CC1=C(C)N=C(Cl)C=C1
MDL No. :MFCD07368876
InChI Key :BLLSRSWUYXEXNF-UHFFFAOYSA-N
Pubchem ID :44754867

Safety of [ 884495-36-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 884495-36-7 ]

* 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.

  • Upstream synthesis route of [ 884495-36-7 ]

[ 884495-36-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 132606-40-7 ]
  • [ 68-12-2 ]
  • [ 884495-36-7 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With n-butyllithium In diethyl ether at -78 - -70℃; for 0.5 h;
Stage #2: at -78 - 20℃; for 1.5 h;
To a 3 L 3-neck flask was added Et2O followed by 2-chloro-6-methyl-5- bromopyridine (56.97 g, 0.28 mol). The mixture was cooled to -78 0C and n-BuLi (132 mL, 0.33 mol) was added dropwise with an addition funnel while maintaining the pot temperature below -70 0C. The mixture was agitated at -78 0C for 30 min, DMF (43 mL, 0.56 mol) was added dropwise at -78 0C then the cooling bath was removed and the reaction was agitated at rt for 1.5 h and quenched with brine (300 mL). The layers were separated and the aqueous layer was extracted with Et2O (150 mL). The combined organic layers were neutralized with cone. HCl to pH -3-4 followed by saturated aqueous NaHCO3 (300 mL). The layers were separated and the organic layer was concentrated to dryness. The product was recrystallized from Et2O/hexane (200 mL, 1 : 1) to afford a light yellow crystalline solid (19 g). The filtrate was concentrated and purified by column chromatography (EtOAc/hexane, 1 :9) to give another crop of product (13 g). Combined yield was 71percent. 1H NMR (CDCl3) δ 2.87 (s, 3H), 7.35 (d, IH, J= 9.0 Hz), 8.07 (d, IH, J= 9.0 Hz), 10.31 (s, IH).
References: [1] Patent: WO2007/22371, 2007, A2, . Location in patent: Page/Page column 50.
[2] Patent: WO2014/28669, 2014, A1, . Location in patent: Paragraph 00328.
  • 2
  • [ 66909-36-2 ]
  • [ 884495-36-7 ]
References: [1] Patent: WO2009/58923, 2009, A1, . Location in patent: Page/Page column 16.
 

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