Thionyl Chloride → 2-(Chloromethyl)-5-methylpyridine hydrochloride

HRID 1620798Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[N:6][CH:7]=1.S(Cl)([Cl:12])=O>>[ClH:12].[Cl:12][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 12325387(5-Methylpyridin-2-yl)methanol

Product 1

HCID 233137952-(Chloromethyl)-5-methylpyridine hydrochloride

Procedure

Oxidation of 2,5-dimethylpyridine provides 2,5-dimethylpyridine N-oxide. Treatment of 2,5-dimethylpyridine N-oxide with acetic anhydride followed by base, such as, sodium hydroxide, provides (5-methyl-pyridin-2-yl)-methanol. (5-Methyl-pyridin-2-yl)-methanol is then treated with thionyl chloride to provide 2-chloromethyl-5-methyl-pyridine hydrochloride.

Sources & evidence

ORD record: ord-120755eb985844e7aa85f20422821353
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772495B2

Reaction notes

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