Phosphorus oxychloride → 4-Chloro-5,8-difluoro-2-methyl-quinoline

HRID 47424Notes

Reaction equation

HRID 47424 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]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178428858HCID 178428858, compound

Product 1

HCID 227451704-Chloro-5,8-difluoro-2-methyl-quinoline

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

  1. customexcess phosphoryl chloride removed at reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with sodium hydrogen carbonate
  4. dry with materialdried (Na2SO4) and solvent
  5. 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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