Phosphorus oxychloride → 3-Isobutyryl-4-chloro-8-methoxyquinoline

HRID 1382333Notes

Reaction equation

HRID 1382333 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)([Cl:21])=O>C(Cl)(Cl)Cl>[Cl:21][C:15]1[C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:1](=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 102639013-isobutyryl-8-methoxy-4(1H)-quinolone

Product 1

HCID 100841433-Isobutyryl-4-chloro-8-methoxyquinolineYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Isobutyryl-8-methoxy-4(1H)-quinolone (8.31 g, 0.034 mol) was heated under reflux in a mixture of phosphorus oxychloride (20 ml) and chloroform (30 ml) for 30 minutes. The mixture was evaporated and the residue was partitioned between dichloromethane and sodium hydrogen carbonate solution. The organic solution was washed with sodium hydrogen carbonate solution, water and brine, dried, filtered and evaporated to give 4-chloro-3-isobutyryl-8-methoxyquinoline as a brown oil (6.4 g, 71%).

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between dichloromethane and sodium hydrogen carbonate solution
  3. washThe organic solution was washed with sodium hydrogen carbonate solution, water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ab474e0496fc42fe8c0c616e67028add
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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