7-methoxyquinoline synthesis
- 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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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
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4964-76-5
74 suppliers
$105.00/100mg