ChemicalBook CAS DataBase List 2-CHLOROMETHYL-4-METHYLPYRIDINE

2-CHLOROMETHYL-4-METHYLPYRIDINE synthesis

5synthesis methods

Product Name:2-CHLOROMETHYL-4-METHYLPYRIDINE
CAS Number:38198-16-2
Molecular formula:C7H8ClN
Molecular Weight:141.6

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Yield:38198-16-2 72.1%

Reaction Conditions:

Stage #1: (4-methyl-2-pyridinyl)methanolwith thionyl chloride in dichloromethane; for 0.0833333 h;Heating / reflux;
Stage #2: with sodium hydrogencarbonate in diethyl ether;water;

Steps:

11.1.4

A mixture solution of (4-methyl-pyridine-2-yl)-methanol (410 mg, 3.33 mmol) described in Manufacturing Example 11-1-3, thionyl chloride (0.49 mL, 6.66 mmol) and methylene chloride (10 mL) was stirred under reflux for 5 minutes. The reaction solution was allowed to room temperature and concentrated under a reduced pressure. The resulting residue was partitioned into diethyl ether and saturated sodium bicarbonate solution. The organic layer was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (340 mg, 72.1%). ¹H-NMR Spectrum (DMSO-d₆) δ (ppm): 2.37 (3H, s), 4.72 (2H, s), 7.20 (1H, d, J=5.2 Hz), 7.38 (1H, s), 8.40 (1H, d, J=5.2 Hz).

References:

US2007/105904,2007,A1 Location in patent:Page/Page column 62