ChemicalBook CAS DataBase List 2-METHOXY-3-CHLOROMETHYL PYRIDINE

2-METHOXY-3-CHLOROMETHYL PYRIDINE synthesis

4synthesis methods

Product Name:2-METHOXY-3-CHLOROMETHYL PYRIDINE
CAS Number:162046-62-0
Molecular formula:C7H8ClNO
Molecular Weight:157.6

112197-16-7
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$9.00/100mg

162046-62-0
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$250.00/500mg

Yield:162046-62-0 93%

Reaction Conditions:

with thionyl chloride in dichloromethane at 20; for 1 h;

Steps:

2 12.2 3-(Chloromethyl)-2-methoxypyridine (45)
Alcohol 44 (1.0 g, 7.2 mmol) was dissolved in 35 ml dichloromethane.
Thionyl chloride (9.4 ml, 18 mmol) was added drop-wise and with stirring and the mixture was stirred for 1 h at room temperature.
The mixture was concentrated under reduced pressure.
The residue was re-suspended in dichloromethane and saturated sodium bicarbonate solution was added carefully.
The mixture was stirred for 10 min and the organic phase was then separated, dried over magnesium sulphate, filtered and evaporated to give 45 (1.05 g, 6.7 mmol, 93% yield) as a pale yellow oil.
Purity 95%. ¹H NMR (300 MHz, CDCl₃) δ ppm 4.01 (s, 3H, MeO), 4.60 (s, 2H, CH₂), 6.90 (dd, J = 5.1, 7.0 Hz, 1H, H-5), 7.65 (d, J = 7.1 Hz, 1H, H-4), 8.13 (d, J = 4.7 Hz, 1H, H-6). UPLC/MS (3 min) retention time 1.46 min. LRMS: m/z no ionization.

References:

Buil, Maria Antonia;Calbet, Marta;Castillo, Marcos;Castro, Jordi;Esteve, Cristina;Ferrer, Manel;Forns, Pilar;González, Jacob;López, Sara;Roberts, Richard S.;Sevilla, Sara;Vidal, Bernat;Vidal, Laura;Vilaseca, Pere [European Journal of Medicinal Chemistry,2016,vol. 113,p. 102 - 133]

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67367-26-4 Synthesis