3-(Chloromethyl)pyridine hydrochloride → HCID 19088793, compound

Participants

Reaction Conditions

Reaction Steps

2-Morpholinyl-6-(4-hydroxyphenyl)-4-pyrone, as prepared in Example 5, (273 mg, 1.0 mmole) was suspended in 6 ml dimethylformamide in a 25 ml one neck round bottom flask under nitrogen. The suspension was treated with sodium hydride suspension (192 mg, 4.0 mmole) and the reaction mixture was warmed to 60° C. for 40 minutes. The reaction was treated with 3-picolyl chloride hydrochloride (492 mg, 3.0 mmole) and the mixture was stirred 2 hours at 60° C. The reaction was poured into 50 ml 2N sodium hydroxide/ice and the mixture was extracted with 4×20 ml dichloromethane. The combined organics were washed with 4×25 ml 50% saturated sodium chloride and were dried over magnesium chloride. The dried organics were concentrated in vacuo to a yellow solid. The crude material was recrystallized twice from ethyl acetate to provide 229 mg (62%) of Compound 5 as a golden crystalline solid.

Provenance & Evidence