Chloroform → 3-Benzoyl-4-chloro-8-methoxyquinoline

HRID 1382272Notes

Reaction equation

HRID 1382272 reaction equation
[C:1]([C:9]1[C:18](=O)[C:17]2[C:12](=[C:13]([O:20][CH3:21])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].C(Cl)(Cl)[Cl:28]>P(Cl)(Cl)(Cl)=O>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[Cl:28])=[CH:16][CH:15]=[CH:14][C:13]=2[O:20][CH3:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 516892Sodium BicarbonateHCID 117783533-benzoyl-8-methoxy-4(1H)-quinolone

Product 1

HCID 100860183-Benzoyl-4-chloro-8-methoxyquinolineYield 100%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-Benzoyl-8-methoxy-4(1H)-quinolone (3.2 g, 0.011 mol) was heated under reflux in a mixture of chloroform (50 ml) and phosphorus oxychloride (7 ml) for 45 minutes. The mixture was cooled and poured into a stirred mixture of sodium hydrogen carbonate solution, ice and chloroform. The organic phase was separated, washed with sodium hydrogen carbonate solution, water and brine. The dried solution was filtered and evaporated to afford 3-benzoyl-4-chloro-8-methoxyquinoline as a yellow oil (3.5 g, 100%).

Workup

  1. temperatureThe mixture was cooled
  2. customThe organic phase was separated
  3. washwashed with sodium hydrogen carbonate solution, water and brine
  4. filtrationThe dried solution was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-c82f5f1b150b4d09b96d35d9a0831676
Source dataset
uspto-grants-1989_02
Patent number
US04806549

Reaction notes

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