Reacción #433776

Ecuación de reacción

Compound 19

1-(4-Fluorobenzyl)-4-hydroxy-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid cyclohexylamide

phosphorus oxychloride

→

yellow solids

Rendimiento 47.0%

4-Chloro-1-(4-fluorobenzyl)-6-methyl-2-oxo-1,2-dihydro-quinoline-3-carbonitrile

Rendimiento 47.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated under reduced pressure
2. 2
   OtroThe solids formed
3. 3
   Filtraciónwere filtered
4. 4
   Lavadowashed by water
5. 5
   Otropurified by flash chromatography
6. 6
   Lavadoeluting with 1% methanol in dichloromethane

Procedimiento

A solution of Compound 19 (5 g, 12.24 mmol) in 30 mL neat phosphorus oxychloride was heated at 100° C. for 3 h. The solvent was evaporated under reduced pressure. The residue was suspended in ice water and neutralized by solid sodium bicarbonate. The solids formed were filtered, washed by water, and purified by flash chromatography eluting with 1% methanol in dichloromethane to yield 1.90 g (47%) of yellow solids. M.P. 206° C. 1H NMR (DMSO-d6): δ 2.40 (s, 3H), 5.52 (s, 2H), 7.12–7.15 (m, 2H), 7.30–7.33 (m, 2H), 7.46 (d, J=8.7 Hz, 1H), 7.64 (dd, J=1.2, 8.7 Hz, 1H), 7.89 (d, J=1.2 Hz, 1H). EIMS m/z 327 (M+1).

Fuente