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Chemical Structure| 16347-06-1

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Product Details of [ 16347-06-1 ]

CAS No. :16347-06-1
Formula : C8H10N2O2
M.W : 166.18
SMILES Code : O=C(NCCO)C1=NC=CC=C1
MDL No. :N/A
InChI Key :SIUMVFGIULAFNI-UHFFFAOYSA-N
Pubchem ID :2045999

Safety of [ 16347-06-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 16347-06-1 ]

* 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 [ 16347-06-1 ]

[ 16347-06-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 119165-69-4 ]
  • [ 16347-06-1 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 17 h; General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4-CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield.
References: [1] Heterocycles, 2017, vol. 94, # 6, p. 1133 - 1142.
  • 2
  • [ 2524-52-9 ]
  • [ 141-43-5 ]
  • [ 16347-06-1 ]
YieldReaction ConditionsOperation in experiment
92% at 20 - 55℃; for 18 h; General procedure: For the synthesis of the hydroxylated precursors, ethanolamine (1.5 mmol) was added slowly to the esters (1 mmol) at 55°C and stirred for 3 h. The reaction mixture was stirred at room temperature for 15 h. The residue was purified by silica gel column chromatography (eluent/ethyl acetate/hexane 8:2) or recrystallized from ethyl acetate. The progress of the reaction was monitored by TLC.`
References: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2783 - 2790.
[2] Journal of Organic Chemistry, 1981, vol. 46, # 13, p. 2824 - 2826.
[3] Organic Letters, 2016, vol. 18, # 14, p. 3434 - 3437.
  • 3
  • [ 119165-69-4 ]
  • [ 84555-18-0 ]
  • [ 16347-06-1 ]
YieldReaction ConditionsOperation in experiment
72% at 20℃; for 21 h; General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4-CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield.
25% at 20℃; for 17 h; General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4-CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield.
References: [1] Heterocycles, 2017, vol. 94, # 6, p. 1133 - 1142.
[2] Heterocycles, 2017, vol. 94, # 6, p. 1133 - 1142.
  • 4
  • [ 119165-69-4 ]
  • [ 16347-06-1 ]
  • [ 717138-97-1 ]
YieldReaction ConditionsOperation in experiment
23% With pyridine; pyridinium perbromide hydrobromide In methanol at 20℃; for 16 h; General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4-CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield.
References: [1] Heterocycles, 2017, vol. 94, # 6, p. 1133 - 1142.
  • 5
  • [ 109-04-6 ]
  • [ 201230-82-2 ]
  • [ 141-43-5 ]
  • [ 16347-06-1 ]
References: [1] Organic Letters, 2014, vol. 16, # 16, p. 4296 - 4299.
  • 6
  • [ 119165-69-4 ]
  • [ 1121-60-4 ]
  • [ 84555-18-0 ]
  • [ 16347-06-1 ]
YieldReaction ConditionsOperation in experiment
23% at 20℃; for 14 h; General procedure: To a solution of 2-(2’-pyridyl)-1,3-oxazoline (1, 37 mg, 0.25 mmol) and pyridine (80 L, 1.0 mmol) in H2O (6 mL), was added pyridinium hydrobromide perbromide (320 mg, 1.0 mmol) at room temperature. After stirring for 23 h at rt, the reaction mixture was treated with 0.5 M aq Na2S2O3 (10 mL), 1.0 M NaHCO3 (15 mL) and extracted with EtOAc (60 mL). The organic layer was washed with 0.5 M aq Na2S2O3 and successively washed with saturated aq NaCl, and dried over MgSO4. After removal ofsolvent in vacuo, the residue was purified by column chromatography on silica gel (Wako C-200) with CCl4, CCl4-CHCl3 (2:1 v/v). Cyanomethyl 2-pyridinecarboxylate (2, 38 mg, 0.23 mmol) was obtained in 92percent yield.
References: [1] Heterocycles, 2017, vol. 94, # 6, p. 1133 - 1142.
  • 7
  • [ 29745-44-6 ]
  • [ 141-43-5 ]
  • [ 16347-06-1 ]
References: [1] Patent: US4764522, 1988, A, .
 

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