METHYL QUINOLINE-6-CARBOXYLATE Chemical Properties

Melting point:

88 °C

Boiling point:

315.1±15.0 °C(Predicted)

Density 

1.210±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.06±0.10(Predicted)

color 

White to Light yellow to Dark green

InChI

InChI=1S/C11H9NO2/c1-14-11(13)9-4-5-10-8(7-9)3-2-6-12-10/h2-7H,1H3

InChIKey

XSRWQTDEIOHXSL-UHFFFAOYSA-N

SMILES

N1C2C(=CC(C(OC)=O)=CC=2)C=CC=1

CAS DataBase Reference

38896-30-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29334900

METHYL QUINOLINE-6-CARBOXYLATE Usage And Synthesis

Chemical Properties

White solid

Synthesis

At 0 °C, 6.0 mmol of thionyl chloride was slowly added dropwise to a 5 mL methanol solution containing 2.0 mmol of 6-quinoline carboxylic acid. Subsequently, the reaction mixture was warmed up to 50 °C with continuous stirring for 12 hours. Upon completion of the reaction, 30 mL of saturated aqueous NaHCO3 solution was added to the mixture to neutralize the reaction. The reaction mixture was extracted three times using 30 mL of dichloromethane and the organic phases were combined. The organic phase was dried over anhydrous MgSO4 and filtered to remove the desiccant. The organic solvent was removed by concentration under reduced pressure to give 6-(methoxycarbonyl)quinoline as a white solid in 98% yield.

References

[1] Heterocycles, 2011, vol. 83, # 7, p. 1649 - 1658
[2] Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10770 - 10776
[3] Patent: WO2015/160125, 2015, A1. Location in patent: Paragraph 143-145
[4] Chemistry - A European Journal, 2015, vol. 21, # 48, p. 17200 - 17204
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6570 - 6580

METHYL QUINOLINE-6-CARBOXYLATE(38896-30-9)Related Product Information

• 6-Quinazolinecarboxylic acid (9CI)
• QUINOXALINE-5-CARBOXYLIC ACID
• 6-Quinazolinamine (9CI)
• 4-HYDROXY-2-METHYLQUINOLINE-6-CARBOXYLIC ACID ETHYL ESTER
• Methyl 3-isoquinolinecarboxylate
• METHYL QUINOLINE-6-CARBOXYLATE
• METHYL 4-CHLORO-6-METHYL-QUINOLINE-2-CARBOXYLATE
• methyl quinoline-3-carboxylate
• Methyl 4-(4'-fluorophenyl)-2-(cyclopropyl)-3-quinolinecarboxylate
• QUINOLINE-6-CARBOXYLIC ACID ETHYL ESTER
• ETHYL 4-CHLORO-2-(TRIFLUOROMETHYL)QUINOLINE-6-CARBOXYLATE
• METHYL QUINOLINE-4-CARBOXYLATE
• Methyl quinoline-5-carboxylate
• methyl quinoline-2-carboxylate
• 3-ALLYL-4-HYDROXY-2-METHYL-QUINOLINE-6-CARBOXYLIC ACID ETHYL ESTER
• AURORA 18632
• AURORA 18635
• AURORA 18631