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

HRID 1382320Notes

Reaction equation

HRID 1382320 reaction equation
[CH:1]1([C:7]([C:9]2[C:18](=O)[C:17]3[C:12](=[C:13]([O:20][CH3:21])[CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)[Cl:23]>P(Cl)(Cl)(Cl)=O>[Cl:23][C:18]1[C:17]2[C:12](=[C:13]([O:20][CH3:21])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[C:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 100167833-cyclohexylcarbonyl-8-methoxy-4(1H)-quinolone

Product 1

HCID 117225423-Cyclohexylcarbonyl-4-chloro-8-methoxyquinolineYield 90%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

3-Cyclohexylcarbonyl-8-methoxy-4(1H)-quinolone (5.8 g, 0.02 mol) was heated under reflux in a mixture of chloroform (100 ml) and phosphorus oxychloride (15 ml) for 2.5 hours. The reaction mixture was partitioned between chloroform, ice and sodium hydrogen carbonate solution (100 g in 1.5 l) and the organic solution was washed with sodium hydrogen carbonate solution and brine. The chloroform solution was dried and evaporated to give 4-chloro-3-cyclohexylcarbonyl-8-methoxy-quinoline (5.5 g, 90%) as an oil.

Workup

  1. customThe reaction mixture was partitioned between chloroform, ice and sodium hydrogen carbonate solution (100 g in 1.5 l)
  2. washthe organic solution was washed with sodium hydrogen carbonate solution and brine
  3. dry with materialThe chloroform solution was dried
  4. customevaporated

Sources & evidence

ORD record
ord-3417969d322f4437a081042f75da24ac
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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