Identification | Back Directory | [Name]
Methyl 7-quinolinecarboxylate | [CAS]
51552-68-2 | [Synonyms]
Methyl 7-quinolinecarboxylate Methyl quinoline-7-carboxylate Quinoline-7-carboxylic acid methyl ester 7-Quinolinecarboxylic acid, methyl ester | [Molecular Formula]
C11H9NO2 | [MDL Number]
MFCD18417763 | [MOL File]
51552-68-2.mol | [Molecular Weight]
187.19 |
Chemical Properties | Back Directory | [Boiling point ]
315.1±15.0 °C(Predicted) | [density ]
1.210±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
2.95±0.14(Predicted) | [Appearance]
Off-white to light yellow Solid |
Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of methyl 7-quinolinecarboxylate from methanol and 7-(trifluoromethyl)quinoline: a mixture of 7-(trifluoromethyl)quinoline (8.9 g, 1 eq.) and 35.6 mL of 10% fuming sulfuric acid was heated at 150 °C for 3 hours, and subsequently cooled to room temperature. To the reaction mixture was added 90 mL of methanol and heated at 80 °C overnight. Upon completion of the reaction, the methanol was removed by distillation. The residue was dissolved in 200 mL of water, neutralized with sodium carbonate solution and subsequently extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was washed with petroleum ether to afford methyl 7-quinolinecarboxylate (7.4 g, 88% yield) as a white solid. | [References]
[1] Patent: US2010/234340, 2010, A1. Location in patent: Page/Page column 21 [2] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 1, p. 59 - 68 [3] Patent: US2004/204455, 2004, A1. Location in patent: Page/Page column 21 [4] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 10, p. 1403 - 1408 [5] Patent: US2008/275037, 2008, A1. Location in patent: Page/Page column 33 |
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