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[ CAS No. 74650-72-9 ] {[proInfo.proName]}

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Chemical Structure| 74650-72-9
Chemical Structure| 74650-72-9
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Product Details of [ 74650-72-9 ]

CAS No. :74650-72-9 MDL No. :
Formula : C7H7ClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 186.60 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 74650-72-9 ]

* 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 [ 74650-72-9 ]
  • Downstream synthetic route of [ 74650-72-9 ]

[ 74650-72-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 74650-72-9 ]
  • [ 791-28-6 ]
  • [ 74650-73-0 ]
YieldReaction ConditionsOperation in experiment
86% With trifluoromethylsulfonic anhydride In dichloromethane (E)
Preparation of 2-chloro-5-methoxynicotinonitrile
Into a flame dried flask under N2 was placed triphenylphosphine oxide (12.0 g, 0.04 mol) and CH2 Cl2 (50 mL) and the mixture cooled to 0°-4° C. A solution of triflic anhydride (6.75 ml, 0.04 mol) in CH2 Cl2 (80 mL) was added dropwise.
After the addition, the solution was stirred for 15 min. and 2-chloro-5-methoxynicotinamide (8.0 g, 0.04 mol) was added portionwise over 15 minutes.
The mixture was allowed to warm to room temperature with stirring overnight, poured into saturated Na2 CO3 solution and extracted with CHCl3 (2*).
After concentration, the residue was chromatographed on silica gel and the product eluted with CHCl3 to yield 6.2 g (86percent) of 2-chloro-5-methoxynicotinonitrile 1 H NMR (CDCl3) δ3.9 (3H, s), 7.5 (1H, d, J=3) and 8.3 (1H, d, J=3); (nujol) 2250 cm- 1.
86% With trifluoromethylsulfonic anhydride In dichloromethane (E)
Preparation of 2-chloro-5-methoxynicotinonitrile
Into a flame dried flask under N2 was placed triphenylphosphine oxide (12.0 g, 0.04 mol) and CH2 Cl2 (50 mL) and the mixture cooled to 0°-4° C. A solution of triflic anhydride (6.75 ml, 0.04 mol) in CH2 Cl2 (80 mL) was added dropwise.
After the addition, the solution was stirred for 15 min. and 2-chloro-5-methoxynicotinamide (8.0 g, 0.04 mol) was added portionwise over 15 minutes.
The mixture was allowed to warm to room temperature with stirring overnight, poured into saturated Na2 CO3 solution and extracted with CHCl3 (2X).
After concentration, the residue was chromatographed on silica gel and the product eluted with CHCl3 to yield 6.2 g (86percent) of 2-chloro-5-methoxynicotinonitrile 1 H NMR (CDCl3) δ 3.9 (3H, s), 7.5 (1H, d, J=3) and 8.3 (1H, d, J=3); (nujol) 2250 cm-1.
Reference: [1] Patent: US4329351, 1982, A,
[2] Patent: US4374140, 1983, A,
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  • [ 74650-73-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 445 - 448
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