Sodium hydride → HCID 53650858, compound

Participants

Reaction Steps

97% sodium hydride (2.72 g. 0.11 mol) was suspended in THF (100 ml) under nitrogen and a solution of N-(2-hydroxyethyl)morpholine (14.4 g, 0.11 mol) in THF (15 ml) was added in portions. When hydrogen evolution had ceased, a solution of 2,3,5-trichloropyridine (18.2 g, 0.10 mol) in THF (25 ml) was added at such a rate as to maintain a gentle reflux. The reaction mixture was refluxed for 2 hours and the solvent was subsequently removed in vacuo. The residue was taken up in water/CH2Cl2, the organic layer was separated and the solvent was removed in vacuo to afford 26.3 g (94.9%) of 3.5-dichloro-2-[2-(4-morpholinyl]ethoxy]pyridine as a crystalline solid.

Provenance & Evidence