4-Hydroxy-6-methoxyquinoline-3-carbonitrile synthesis
- Product Name:4-Hydroxy-6-methoxyquinoline-3-carbonitrile
- CAS Number:13669-61-9
- Molecular formula:C11H8N2O2
- Molecular Weight:200.19
![Benzoic acid, 2-[(E)-[(dimethylamino)methylene]amino]-5-methoxy-, methyl ester](/CAS/20210305/GIF/872714-53-9.gif)
Yield:13669-61-9 85%
Reaction Conditions:
Stage #1: acetonitrilewith n-butyllithium in tetrahydrofuran at -72; for 1 h;
Stage #2: (E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate in tetrahydrofuran at -72 - 20;
Stage #3: with acetic acid in tetrahydrofuran; for 1 h;
Steps:
2.b
b) 4-Hydroxy-6~(methyloxy)-3-quinolinecarbonitrile; To a cold solution of acetonitrile (2 mL, 38 mmol, 2.8 eq) in THF (30 mL) at -72 0C (Dry-ice/IPA) was added dropwise nBuLi (12 mL, 30 mmol, 2.2 eq) under argon atmosphere. The reaction mixture became an orange suspension after 1 h. A solution of methyl 2-{[(1/Ξ)-(dimethylamino)methylidene]amino}-5-(methyloxy)benzoate (3.2 g, 13.6 mmol, 1 eq) in THF (30 mL) was then added dropwise while the internal temperature was maintained at -72 0C. The resulting mixture was slowly warmed to RT overnight. To the resulting light-brown suspension was added glacial acetic acid (6 mL) with slight cooling. After stirring for 1 h, the suspension was then quenched with water (60 mL) and filtered to give the titled compound (2.3 g, 85 % yield).
References:
WO2006/2047,2006,A2 Location in patent:Page/Page column 62
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