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Type HazMat fee for 500 gram (Estimated)
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Chemical Structure| 853109-24-7 Chemical Structure| 853109-24-7

Structure of 853109-24-7

Chemical Structure| 853109-24-7

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Product Details of [ 853109-24-7 ]

CAS No. :853109-24-7
Formula : C8H8ClNO3
M.W : 201.61
SMILES Code : COC(C1=C(Cl)N(C)C(C=C1)=O)=O
MDL No. :MFCD26395032

Safety of [ 853109-24-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H311-H331
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 853109-24-7 ]

* 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.

  • Downstream synthetic route of [ 853109-24-7 ]

[ 853109-24-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 74-88-4 ]
  • [ 853109-24-7 ]
  • [ 95652-77-0 ]
YieldReaction ConditionsOperation in experiment
62% To a solution of 2-chloro-6-oxo-l,6-dihydro-pyridine-3- carboxylic acid (0.644 g, 3.71 mmol) in DMF (20 mL) was added lithium hydride (95%, EPO <DP n="78"/>0.078 g, 9.28 mmol) and the reaction mixture was stirred for 40 minutes under N2. Methyl iodide (0.508 mL, 1.16 g, 8.16 mmol) was then added and the reaction mixture was stirred for an additional 45 minutes. The reaction mixture was quenched with 2 M HCl until the pH was 6-7. The reaction mixture was diluted with EtOAc and saturated NaCl and the layers separated. The aqueous layer was back extracted with EtOAc (Ix). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to yield a crude yellow solid. HPLC analysis showed two products in a 4:1 ratio that were separated by flash column chromatography (methylene chloride/EtOAc, 15:1 to 10:1) to give 0.466 g (62%) pure desired product as a white crystalline solid. The minor product was also isolated as a pale yellow crystalline solid and identified as the regioisomer 2-chloro-6-methoxy-nicotinic acid methyl ester; To a solution of 2-chloro-6-oxo-l,6-dihydropyridine-3-carboxylic acid (0.644 g, 3.71 mmol) in DMF (20 mL) was added lithium hydride (95%, 0.078 g, 9.28 mmol) and the reaction mixture was stirred for 40 minutes under N2. Methyl iodide (0.508 mL, 1.16 g, 8.16 mmol) was then added and the reaction mixture was stirred for an additional 45 minutes. The reaction mixture was quenched with 2 M HCl until the pH was 6-7. The reaction mixture was diluted with EtOAc and saturated NaCl and the layers were separated. The aqueous layer was back-extracted with EtOAc (Ix). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to yield a crude yellow solid. HPLC analysis showed two products in a 4:1 ratio that were separated by flash column chromatography (methylene chloride/EtOAc, 15:1 to 10:1) to give 0.466 g (62%) pure desired product as a white crystalline solid. The minor product was also isolated as a pale yellow crystalline solid and identified as the regioisomer methyl 2-chloro-6- methoxynicotinate .
 

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