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Chemical Structure| 289686-74-4 Chemical Structure| 289686-74-4

Structure of 289686-74-4

Chemical Structure| 289686-74-4

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Product Details of [ 289686-74-4 ]

CAS No. :289686-74-4
Formula : C9H10ClNO2
M.W : 199.63
SMILES Code : O=C(N(OC)C)C1=CC=CC=C1Cl
MDL No. :MFCD02684306
InChI Key :ZBRUSXSYQDZHQM-UHFFFAOYSA-N
Pubchem ID :18185370

Safety of [ 289686-74-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 289686-74-4 ]

* 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.

  • Upstream synthesis route of [ 289686-74-4 ]

[ 289686-74-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 108-89-4 ]
  • [ 289686-74-4 ]
  • [ 216076-11-8 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -78 - 0℃; for 0.5 h;
Stage #2: at -78 - 20℃;
To lithium diisopropyl amide (6.5 mL, 1.6 M in cyclohexane, 10.4 mmol) in THF (20.0 mL) at -78 °C was added a solution of 4-picoline (1.07g mL, 11.5 mmol) in THF (10.0 mL) dropwise. The dry ice bath was removed. The reaction mixture was stirred at 0 "C for 30 minutes, and cooled back to -78 °C. A solution of 2-chloro-N-methoxy-N- methylbenzamide (21) (2.39 g, 12 mmol) in THF (10.0 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. White solid was filtered off and dissolved in ethyl acetate. The organic phase was washed with water, brine, dried over dried magnesium sulfate and concentrated under vacuum to give l-(2-chlorophenyl)-2-(pyridin-4-yl)ethanone (22) (1.09 g, 4.7 mmol, 47percent) as white solid.
47%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -78 - 20℃;
Stage #2: at -78 - 20℃;
l-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanone (22): To lithium diisopropyl amide (6.5 mL, 1.6 M in cyclohexane, 10.4 mmol) in THF (20.0 mL) at -78 0C was added a solution of 4-picoline (1.07g mL, 1 1.5 mmol) in THF (10.0 mL) dropwise. The dry ice bath was removed. The reaction mixture was stirred at 0 0C for 30 minutes, and cooled back to -78 0C. A solution of 2-chloro-N-methoxy-N-methylbenzamide (21) (2.39 g, 12 mmol) in THF (10.0 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. White solid was filtered off and dissolved in ethyl acetate. The organic phase was washed with water, brine, dried over dried magnesium sulfate and concentrated under vacuum to give l-(2-chlorophenyl)-2- (pyridin-4-yl)ethanone (22) (1.09 g, 4.7 mmol, 47percent) as white solid.
References: [1] Patent: WO2009/91759, 2009, A1, . Location in patent: Page/Page column 49.
[2] Patent: WO2009/91760, 2009, A1, . Location in patent: Page/Page column 41.
 

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