Phosphorus oxychloride → 3-Butyryl-6-benzyloxy-4-chloro-8-methoxy quinoline

HRID 1885193Notes

Reaction equation

HRID 1885193 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([O:26][CH3:27])[CH:11]=[C:12]([O:17][C:18](=O)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:30])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:30])=[CH:13][C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:11][C:10]=2[O:26][CH3:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 104065273-butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinolone

Product 1

HCID 198802873-Butyryl-6-benzyloxy-4-chloro-8-methoxy quinoline

Procedure

3-Butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinolone (18.0 g) was heated under reflux in phosphorus oxychloride (100 ml) for 40 minutes. The solvent was evaporated and the residue dissolved in dichloromethane and poured into a vigorously stirred mixture of ice and sodium hydrogen carbonate solution. The organic phase was washed with sodium hydrogen carbonate solution, dried, filtered and evaporated to give 3-butyryl-6-benzyloxy-4-chloro-8-methoxy quinoline as a brown oil (25 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. additionpoured into a vigorously stirred mixture of ice and sodium hydrogen carbonate solution
  4. washThe organic phase was washed with sodium hydrogen carbonate solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ffeb59053f484f92991a4bee1897905b
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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