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Chemical Structure| 58553-48-3 Chemical Structure| 58553-48-3

Structure of 58553-48-3

Chemical Structure| 58553-48-3

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Product Details of [ 58553-48-3 ]

CAS No. :58553-48-3
Formula : C7H6N2O
M.W : 134.14
SMILES Code : N#CC1=NC=C(CO)C=C1
MDL No. :MFCD09029606
InChI Key :UFTHYXJJRHOQGT-UHFFFAOYSA-N
Pubchem ID :12251966

Safety of [ 58553-48-3 ]

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

Application In Synthesis of [ 58553-48-3 ]

* 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.

  • Downstream synthetic route of [ 58553-48-3 ]

[ 58553-48-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 58553-48-3 ]
  • [ 1225380-31-3 ]
YieldReaction ConditionsOperation in experiment
75% With thionyl chloride; In dichloromethane; at 0 - 20℃; for 6.0h; 272 mul (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was dried under a high vacuum. 263 mg (75% of th.) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H).MS (ESIpos): m/z=153/155 (35Cl/37Cl) [M+H]+.LC/MS (method F, ESIpos): Rt=0.75 min, m/z=153/155 (35Cl/37Cl) [M+H]+.
75% With thionyl chloride; In dichloromethane; at 0 - 20℃; for 6.0h; Example 31A5-(Chloromethyl)pyridine-2-carbonitrile hydrochloride; 272 mul (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous dichloromethane at 0 C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained in this way was dried under high vacuum. 263 mg (75% of theory) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H).MS (ESIpos): m/z=153/155 (35Cl/37Cl) [M+H]+.LC/MS (method F, ESIpos): Rt=0.75 min, m/z=153/155 (35Cl/37Cl) [M+H]+.
75% With thionyl chloride; In dichloromethane; at 0 - 20℃; for 6.0h; Example 45A 5-(Chloromethyl)pyridine-2-carbonitrile hydrochloride 272 mul (3.73 mmol) of thionyl chloride were added to a solution of 250 mg (1.86 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 5 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 6 h. All the volatile constituents were then removed on a rotary evaporator and the residue obtained was dried under a high vacuum. 263 mg (75% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 8.73 (d, 1H), 7.90 (dd, 1H), 7.72 (d, 1H), 4.63 (s, 2H). MS (ESIpos): m/z=153/155 (35Cl/37Cl) [M+H]+. LC/MS (method F, ESIpos): Rt=0.75 min, m/z=153/155 (35Cl/37Cl) [M+H]+.
  • 2
  • [ 58553-48-3 ]
  • [ 124-63-0 ]
  • [ 421551-72-6 ]
  • [ 1225380-31-3 ]
YieldReaction ConditionsOperation in experiment
48%; 47% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 1.0h; .51 ml (27.14 mmol) of N,N-diisopropylethylamine and 2.87 ml (25.05 mmol) of methanesulphonic acid chloride were added successively to a solution of 2.8 g (20.87 mmol) of <strong>[58553-48-3]5-(hydroxymethyl)pyridine-2-carbonitrile</strong> [A. Ashimori et al., Chem. Pharm. Bull. 1990, 38 (9), 2446-2458] in 50 ml of anhydrous methylene chloride at 0 C. The reaction mixture was then stirred at RT for 1 h. 10 ml of water were then added, the phases were separated and the aqueous phase was extracted twice with approx. 10 ml of methylene chloride each time. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and freed from the solvent on a rotary evaporator. The residue obtained was separated into its components by means of MPLC (silica gel, mobile phase: cyclohexane/ethyl acetate 1:1). 2.12 g (48% of th.) of the title compound (for the analytical data see below) and 1.51 g (47% of th.) of the compound described in Example 40A were obtained.1H-NMR (400 MHz, CDCl3, delta/ppm): 8.76 (d, 1H), 7.93 (dd, 1H), 7.78 (d, 1H), 5.32 (s, 2H), 3.10 (s, 3H).MS (DCI, NH3): m/z=213 [M+H]+, 230 [M+NH4]+.LC/MS (method F, ESIpos): Rt=0.57 min, m/z=213 [M+H]+.
 

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