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Methyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

  • CAS No. 637027-41-9

  • Cat. No. CS-M1951
  • Molecule weight267.67
  • Purity≥98%
  • MDL No.MFCD09032505

*For research and further manufacturing use only, not for direct human use.

Methyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate|CS-M1951

Structure of 637027-41-9

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General Information

  • CAS No. 637027-41-9
  • Cat. No. CS-M1951
  • Purity ≥98%
  • MDL No. MFCD09032505
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₀ClNO₄
  • Molecular Weight 267.67
  • Synonym(s) 3-Quinolinecarboxylic acid, 5-chloro-1,2-dihydro-4-hydroxy-1-Methyl-2-oxo-, Methyl ester
  • SMILES ClC1=C2C(N(C)C(C(C(OC)=O)=C2O)=O)=CC=C1

Description

Methyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate features a sterically hindered quinoline core with orthogonal functional groups enabling selective derivatization. The electron-deficient ring system pairs with a bench-stable hydroxyl and ester handle, facilitating integration into bioactive scaffolds under standard conditions.

Application

Methyl 5-chloro-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate serves as a versatile building block for quinoline-based heterocycles, enabling efficient access to medicinally relevant scaffolds. Its hydroxyl and ester functionalities permit selective derivatization, while the chlorine substituent facilitates subsequent cross-coupling reactions. The compound exhibits bench stability and compatibility with standard purification methods, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • ACTIVE BIOTECH AB Patent: US2004/34227 A1, 2004 ; Location in patent: Page 3 ;
  • Route2

    References

    • Wennerberg, Johan; Bjoerk, Anders; Fristedt, Tomas; Granquis, Bo; Jansson, Karl; Thuvesson, Ingela Organic Process Research and Development, 2007 , vol. 11, # 4 p. 674 - 680
  • Route3

    References

    • ACTIVE BIOTECH AB Patent: WO2003/106424 A1, 2003 ; Location in patent: Page 5 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   68.53
  • LogP   1.6841
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   1

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