Introduction of a new synthetic route about 4-(Chloromethyl)pyridine hydrochloride

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Related Products of 1822-51-1 , The common heterocyclic compound, 1822-51-1, name is 4-(Chloromethyl)pyridine hydrochloride, molecular formula is C6H7Cl2N, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Reference Example 1 Methyl 2-(pyridin-4-yl)methoxybenzoate (Reference Compound 1-(1)) To a solution of methyl salicylate (10 g, 66 mmol) and 4-chloromethylpyridine hydrochloride (11 g, 67 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (19 g, 140 mmol) under ice-cooling, and then the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into an ice water and the aqueous layer was extracted with ethyl acetate (150 mL, twice). The ethyl acetate layer was washed with a saturated brine solution (200 mL), dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness, and the resultant residue was purified with a silica gel column chromatography (hexane/ethyl acetate) and dried to give 12 g (75 %) of the titled compound as a colorless solid. 1H-NMR (300MHz, CDCl3) delta 3.93 (s, 3H), 5.19(s, 2H), 6.97(d, J=8.3Hz, 1H), 7.04(t, J=7.5Hz, 1H), 7.43-7.50(m, 3H), 7.87(dd, J=7.9, 1.8Hz, 1H), 8.63(d, J=6.1Hz, 2H) The following Reference Compounds 1-(2) to (8) were obtained by a production method similar to that of Reference Compound 1-(1) using compounds selected from known compounds, 4-chloromethylquinoline (CAS#5632-17-7;) and 2-acetamido-4-methanesulfonyloxymethylpyridine (CAS#864461-12-1;) and commercially available compounds.

The synthetic route of 1822-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Santen Pharmaceutical Co., Ltd; EP2128156; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem