(2-methoxy-3-quinolinyl)methanol synthesis

4synthesis methods

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

67-56-1 Synthesis