Sodium Carbonate → HCID 66666248, compound

Participants

Reaction Steps

POCl3 (10 ml, 107 mmol) was added dropwise to a mixture of 6,7-diphenyl-1,8-naphthyridine 1-oxide and 2,3-diphenyl-1,8-naphthyridine 1-oxide (Intermediates C) (3 g, 10.06 mmol) at 0° C. The reaction mixture was allowed to warm at room temperature and heated at 100° C. for 2 h. The mixture was poured carefully onto ice/water and the pH was adjusted to pH 8-9 by addition of Na2CO3 (solid) portionwise. The aqueous layer was separated and extracted with DCM (3×150 ml). The organic portions were combined and washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford a brown oil. Purification of the crude oil by chromatography on silica eluting with 0-50% EtOAc in iso-hexane afforded 7-chloro-2,3-diphenyl-1,8-naphthyridine and 5-chloro-2,3-diphenyl-1,8-naphthyridine:

Provenance & Evidence