Methyl 2-Methyl-6-quinolinecarboxylate

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Methyl 2-Methyl-6-quinolinecarboxylate manufacturers

Methyl 2-Methyl-6-quinolinecarboxylate Basic information
Product Name:Methyl 2-Methyl-6-quinolinecarboxylate
Synonyms:Methyl 2-Methyl-6-quinolinecarboxylate;2-Methylquinoline-6-carboxylic acid methyl ester;6-Quinolinecarboxylic acid, 2-methyl-, methyl ester;2-Methyl-6-quinolinecarboxylic acid methyl ester;Methyl 2-Methylquinoline-6-carboxylate
CAS:108166-01-4
MF:C12H11NO2
MW:201.22
EINECS:
Product Categories:
Mol File:108166-01-4.mol
Methyl 2-Methyl-6-quinolinecarboxylate Structure
Methyl 2-Methyl-6-quinolinecarboxylate Chemical Properties
Melting point 103-105 °C
Boiling point 320.3±22.0 °C(Predicted)
density 1.177±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
form solid
pka4.90±0.43(Predicted)
color Light grey
InChIInChI=1S/C12H11NO2/c1-8-3-4-9-7-10(12(14)15-2)5-6-11(9)13-8/h3-7H,1-2H3
InChIKeyKGSIXOOGGCSYTB-UHFFFAOYSA-N
SMILESN1C2C(=CC(C(OC)=O)=CC=2)C=CC=1C
Safety Information
HS Code 2933499090
MSDS Information
Methyl 2-Methyl-6-quinolinecarboxylate Usage And Synthesis
Synthesis
Methanol

67-56-1

2-Methyl-6-quinolinecarboxylic acid

635-80-3

Methyl 2-Methyl-6-quinolinecarboxylate

108166-01-4

Step 2: Synthesis of methyl 2-methylquinoline-6-carboxylate: 2-methyl-6-quinolinecarboxylic acid (3.0 g, 16.20 mmol) was dissolved in methanol (30 mL) at 0°C and concentrated sulfuric acid (3 mL) was added slowly and dropwise. Subsequently, the reaction mixture was warmed to 65°C and stirred continuously for 12 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure. The concentrated residue was extracted by adding dichloromethane and aqueous sodium carbonate to the concentrated residue. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford methyl 2-methylquinoline-6-carboxylate as a brown solid (1.9 g, 59% yield).

References[1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 929 - 931
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227
[3] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4
[4] Patent: WO2013/144737, 2013, A2. Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1. Location in patent: Paragraph 0525
Methyl 2-Methyl-6-quinolinecarboxylate Preparation Products And Raw materials
Raw materialsMethanol-->2-Methyl-6-quinolinecarboxylic acid
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