ChemicalBook CAS DataBase List ethyl 7-methoxyquinoline-3-carboxylate

ethyl 7-methoxyquinoline-3-carboxylate synthesis

6synthesis methods

Product Name:ethyl 7-methoxyquinoline-3-carboxylate
CAS Number:71082-46-7
Molecular formula:C13H13NO3
Molecular Weight:231.25

77156-85-5 Synthesis

Ethyl 4-chloro-7-methoxyquinoline- 3-carboxylate

77156-85-5
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71082-46-7
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Yield: 89%

Reaction Conditions:

with palladium 10% on activated carbon;palladium in ethanol;ethyl acetate

Steps:

D Step D. Ethyl 7-methoxyquinoline-3-carboxylate
Step D.
Ethyl 7-methoxyquinoline-3-carboxylate.
To a solution of ethyl 4-chloro-7-methoxyquinoline-3-carboxylate (1.24 g, 4.67 mmol) in a mixture of EtOAc (30 mL) and ethanol (30 mL) was added 10% Pd/C (10 mg).
The flask was evacuated and filled with nitrogen three times and evacuated and filled with hydrogen three times and stirred overnight.
After filtration through a plug of silica the reaction mixture was concentrated onto silica.
Purification by FCC (SiO₂, 0-10% MeOH/DCM) afforded the title compound as a brown solid (955 mg, 89%).
¹H NMR (400 MHz, CDCl₃) δ 9.37 (d, J=2.0 Hz, 1H), 8.75 (d, J=2.0 Hz, 1H), 7.80 (d, J=9.0 Hz, 1H), 7.47 (d, J=2.3 Hz, 1H), 7.27 (d, J=2.3 Hz, 1H), 4.45 (q, J=7.0 Hz, 2H), 4.01-3.93 (m, 3H), 1.44 (t, J=7.2 Hz, 3H).
[M+H]=232.2.

References:

Basinger, Jillian;Breitenbucher, James;Freestone, Graeme;Gupta, Varsha;Kaplan, Alan;Mak, Chi-Ching;Pratt, Benjamin;Santora, Vincent;Sengupta, Dipanjan;Valdez, Lino US2014/275548, 2014, A1 Location in patent:Paragraph 0362

64-18-6 Synthesis