ChemicalBook--->CAS DataBase List--->108166-01-4

108166-01-4

108166-01-4 Structure

108166-01-4 Structure
IdentificationBack Directory
[Name]

Methyl 2-Methyl-6-quinolinecarboxylate
[CAS]

108166-01-4
[Synonyms]

Methyl 2-Methyl-6-quinolinecarboxylate
Methyl 2-Methylquinoline-6-carboxylate
2-Methylquinoline-6-carboxylic acid methyl ester
6-Quinolinecarboxylic acid, 2-methyl-, methyl ester
[Molecular Formula]

C12H11NO2
[MDL Number]

MFCD02690144
[MOL File]

108166-01-4.mol
[Molecular Weight]

201.22
Chemical PropertiesBack Directory
[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
[pka]

4.90±0.43(Predicted)
[color ]

Light grey
[InChI]

InChI=1S/C12H11NO2/c1-8-3-4-9-7-10(12(14)15-2)5-6-11(9)13-8/h3-7H,1-2H3
[InChIKey]

KGSIXOOGGCSYTB-UHFFFAOYSA-N
[SMILES]

N1C2C(=CC(C(OC)=O)=CC=2)C=CC=1C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H319-H335-H302+H312+H332-H315
[Precautionary statements ]

P280-P301+P312-P362+P364
[HS Code ]

2933499090
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl 2-Methyl-6-quinolinecarboxylate(108166-01-4)1HNMR
Hazard InformationBack Directory
[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
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