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

Melting point:

128-131 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Sparingly)

form 

Solid

color 

White to Off-White

Water Solubility 

Soluble in water.

InChI

InChI=1S/C9H12ClNO.ClH/c1-6-5-11-8(4-10)7(2)9(6)12-3;/h5H,4H2,1-3H3;1H

InChIKey

LCJDHJOUOJSJGS-UHFFFAOYSA-N

SMILES

C1(CCl)=NC=C(C)C(OC)=C1C.[H]Cl

CAS DataBase Reference

86604-75-3(CAS DataBase Reference)

Safety Information

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

3261

WGK Germany 

3

HazardClass 

8

PackingGroup 

II

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

2-Chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride is used as pharmaceutical intermediates. It is an intermediate in the production of the antiulcer agent Omeprazole.

Synthesis

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.

References

[1] Patent: WO2004/9583, 2004, A2. Location in patent: Page 156
[2] Patent: US2005/38076, 2005, A1. Location in patent: Page/Page column 6
[3] Patent: CN107011252, 2017, A. Location in patent: Paragraph 0063; 0064; 0066; 0068; 0072; 0074
[4] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1777 - 1788
[5] Patent: US5292886, 1994, A

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