2-Methyl-5-chloromethylpyridine hydrochloride Chemical Properties

Melting point:

133-135 °C

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light yellow to yellow Solid

2-Methyl-5-chloromethylpyridine hydrochloride Usage And Synthesis

Synthesis

A solution of 6-methyl-3-methanol pyridine (52.2 g, 424 mmol) was prepared by dissolving it in 190 ml of toluene and 60 ml of CHCl3 as starting material. This solution was slowly added dropwise to 44 ml of toluene solution containing SOCl2 (34 ml, 469 mmol), and the internal temperature of the reaction system was controlled to be maintained between 23°C and 35°C during the dropwise addition. After the dropwise addition, the reaction mixture was stirred vigorously at room temperature for 1 hour. Subsequently, all solvents were removed by distillation under reduced pressure with a water pump. The brown precipitate obtained was resuspended with toluene, rapidly filtered and washed three times with toluene. Finally, the product was dried in a desiccator (vacuum via aspirator) to give 5-(chloromethyl)-2-methylpyridine hydrochloride 72.1 g (405 mmol, 96% yield) as a brown solid.

References

[1] Patent: US2005/124586, 2005, A1. Location in patent: Page/Page column 7
[2] Patent: WO2012/82689, 2012, A1. Location in patent: Page/Page column 129
[3] Journal of Medicinal Chemistry, 1991, vol. 34, # 3, p. 1028 - 1036
[4] Patent: US2010/143301, 2010, A1. Location in patent: Page/Page column 108
[5] Patent: WO2015/163485, 2015, A1. Location in patent: Paragraph 0524

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