2-Methoxyquinoline-7-carboxylic acid synthesis

6synthesis methods

Product Name:2-Methoxyquinoline-7-carboxylic acid
CAS Number:1374258-40-8
Molecular formula:C11H9NO3
Molecular Weight:203.19

1374258-39-5 Synthesis

1374258-39-5
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1374258-40-8
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Yield:1374258-40-8 96%

Reaction Conditions:

Stage #1: ethyl 2-methoxyquinoline-7-carboxylatewith water;lithium hydroxide in tetrahydrofuran at 20; for 65 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;water; pH=4;

Steps:

19.3

To a solution of ethyl 2-methoxyquinoline-7-carboxylate (125 mg, 0.54 mmol) in tetrahydrofuran (1.5 mL) was added 2 N aqueous lithium hydroxide (0.81 mL, 1.6 mmol). The reaction was stirred at room temperature for 65 hours. The tetrahydrofuran was removed in vacuo and the residue was acidified to pH=4 with 1 N aqueous hydrochloric acid. The mixture was diluted with water and the resulting precipitate was collected by filtration and dried under vacuum to give the title compound (106 mg, 96%) as a white solid. +ESI (M+H) 204.2; ¹H NMR (400 MHz, CDCl₃, δ): 8.64 (d, J=1.37 Hz, 1H), 8.01-8.04 (m, 1H), 8.01 (s, 1 H), 7.79 (d, J=8.58 Hz, 1H), 7.01 (d, J=8.78 Hz, 1H), 4.09 (s, 3H).

References:

US2012/108619,2012,A1 Location in patent:Page/Page column 36

1451154-40-7 Synthesis