3-(Chloromethyl)pyridine hydrochloride → HCID 67482386, compound

Participants

Reaction Steps

3-Nitro-1H-pyrazole (prepared as in Example 15, 113 mg, 1.00 mmol) was dissolved in N,N-dimethylformamide (5 mL) and cooled in an ice bath. A 60% suspension of sodium hydride in mineral oil (88 mg, 2.2 mmol) was added in portions and the cooling bath was removed. After stirring 1.5 h, a mixture of 3-picolyl chloride hydrochloride (164 mg, 1.00 mmol) in N,N-dimethylformamide (1 mL) was added. The reaction mixture was stirred 65 h, then evaporated in vacuo. The residue was treated with saturated aqueous sodium bicarbonate solution (1 mL) and extracted with chloroform (2×3 mL). The combined organic phases were dried over sodium sulfate and evaporated in vacuo. The residue was stirred in ethyl acetate (50 mL) and filtered. The filtrate was evaporated in vacuo and the remaining material was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; (50% ethyl acetate/hexanes to 100% ethyl acetate) to afford 3-(3-nitro-pyrazol-1-ylmethyl)-pyridine (114 mg, 56%) as a clear, faintly yellow oil which began to solidify over time: LC-MS (ESI) m/e calcd for C9H8N4O2 [M+] 204.06, found 205 [M+H+].

Provenance & Evidence