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

HRID 1382281Notes

Reaction equation

HRID 1382281 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-93c26d57b65f40b8afd2396f967ad0b8
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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