Phosphorus oxychloride → 4-Chloro-5,8-difluoro-2-methyl-quinoline
Reaction equation
O[C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:14])[CH:3]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:14])[CH:3]=1Participants
3
Procedure
4-Hydroxy-5,8-difluoro-2-methylquinoline (5.4 g) in phosphoryl chloride (60 ml) was boiled for 4 h. The mixture was cooled to room temperature, excess phosphoryl chloride removed at reduced pressure, the residue dissolved in ethyl acetate, washed with sodium hydrogen carbonate, dried (Na2SO4) and solvent removed at reduced pressure. The title compound (5.35 g) was isolated as a brown powder. (Method B). 1H NMR δ: 2.61 (3H, s), 7.46 (1H, m), 7.66 (1H, m), 7.81 (1H, s).
Workup
- customexcess phosphoryl chloride removed at reduced pressure
- dissolutionthe residue dissolved in ethyl acetate
- washwashed with sodium hydrogen carbonate
- dry with materialdried (Na2SO4) and solvent
- customremoved at reduced pressure
Sources & evidence
- ORD record
- ord-4b454f3f65ed464db04cba23baf9e15b
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06699879B1
Reaction notes
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