(2-methoxy-3-quinolinyl)methanol synthesis
- Product Name:(2-methoxy-3-quinolinyl)methanol
- CAS Number:1038969-22-0
- Molecular formula:C11H11NO2
- Molecular Weight:189.21
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Yield:1038969-22-0 100%
Reaction Conditions:
with methanol;sodium tetrahydroborate at 0;
Steps:
(2-methoxyquinolin-3-yl)methanol
(2-methoxyquinolin-3-yl)methanol
2-Methoxyquinoline-3-carbaldehyde (1.45 g, 7.75 mmol) was suspended in methanol (20 mL) and the mixture was cooled to 0° C. Sodium borohydride (600 mg, 15.86 mmol) was added, causing bubbling.
The reaction mixture was stirred and gradually warmed to room temperature overnight (let ice bath melt).
The reaction mixture was concentrated, and the crude material was taken up in saturated aqueous bicarbonate solution (50 mL) and extracted with dichloromethane (2*50 mL).
The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the title compound (1.46 g, 7.72 mmol, 100% yield).
1H NMR (500 MHz, DMSO-d6) δ ppm 8.19 (q, J=1.2 Hz, 1H), 7.90 (dd, J=8.0, 1.5 Hz, 1H), 7.82-7.72 (m, 1H), 7.62 (ddd, J=8.4, 6.9, 1.5 Hz, 1H), 7.42 (ddd, J=8.1, 6.9, 1.2 Hz, 1H), 5.44-5.30 (m, 1H), 4.66-4.54 (m, 2H), 4.01 (s, 3H); MS (ESI+) m/z 190 (M+H)+.
References:
US2018/99932,2018,A1 Location in patent:Paragraph 1511; 1521; 1798
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139549-06-7
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$22.00/250mg
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