ChemicalBook CAS DataBase List 7-methoxyquinoline

7-methoxyquinoline synthesis

13synthesis methods

Product Name:7-methoxyquinoline
CAS Number:4964-76-5
Molecular formula:C10H9NO
Molecular Weight:159.18

74-88-4
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4964-76-5
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$105.00/100mg

Yield: 99%

Reaction Conditions:

Stage #1:quinolin-7-ol with sodium hydride in N,N-dimethyl-formamide at 0; for 1 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 1 h;

Steps:

1.a
(a) 7-(Methyloxy)quinoline; A suspension of NaH (3.3g; 137.93mmol) in anhydrous DMF (160ml) was cooled to 0°C with stirring under argon. 7-Quinolinol (8g; 55.17mmol) dissolved in anhydrous DMF (320ml) was added and the mixture was stirred at 0°C under argon for Ih. The mixture was then allowed to warm to rt and MeI (7.8ml; 55.17mmol) was added and the reaction was stirred for Ih. Ice water was then added cautiously and the resulting mixture extracted with EtOAc (3 x 500ml). The organic layer from this extraction was then washed with water (400ml) and brine (400ml). The resulting organic layer was dried with MgSO₄ and solvents removed to afford the desired compound (8.76g; 99%) MS (ES+) m/z 160 (MH⁺).

References:

GLAXO GROUP LIMITED WO2008/9700, 2008, A1 Location in patent:Page/Page column 32