ChemicalBook CAS DataBase List 2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride

2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride synthesis

11synthesis methods

Product Name:2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride
CAS Number:86604-75-3
Molecular formula:C9H13Cl2NO
Molecular Weight:222.11

3,5-Dimethyl-4-methoxy-2-pyridinemethanol

86604-78-6

2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride

86604-75-3

The general procedure for the synthesis of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride from 4-methoxy-3,5-dimethyl-2-hydroxymethylpyridine was as follows: to a solution of 4-methoxy-3,5-dimethyl-2-hydroxymethylpyridine (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added slowly and dropwise thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL). 0.158 mol) to a solution of thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL). The reaction was carried out at room temperature and under argon protection, and the titration process lasted for 30 minutes. After the dropwise addition, the reaction was continued with stirring at room temperature for 30 minutes. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The solid residue obtained was suspended in hexane (200 mL) and the solid was collected by filtration. The solid was washed with hexane (50 mL) and subsequently dried in air to afford 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride 33.3 g (100% yield) as a white solid.

86604-78-6 Synthesis

86604-78-6
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$7.00/5g

86604-75-3
565 suppliers
$10.00/1g

Yield:86604-75-3 100%

Reaction Conditions:

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

Steps:

[2-CHLOROMETHYL-3SS-DIMETHYL-4-METHOXYPYRIDINE] hydrochloride

To a solution [OF 4-METHOXY-3, 5-DIMETHYLPYRIDINEMETHANOL] (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0. [158] mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure. The solid residue was suspended in hexanes (200 mL) and filtered. The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100%) of the title compound as a white solid.

References:

WO2004/9583,2004,A2 Location in patent:Page 156