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

HRID 1382316Notes

Reaction equation

HRID 1382316 reaction equation
[C:1]([C:8]1[C:17](=O)[C:16]2[C:11](=[C:12]([O:19][CH3:20])[CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:28])=O>C(Cl)(Cl)Cl>[Cl:28][C:17]1[C:16]2[C:11](=[C:12]([O:19][CH3:20])[CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 117780603-hexanoyl-8-methoxy-4(1H)-quinolone

Product 1

HCID 101083533-Hexanoyl-4-chloro-8-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3-hexanoyl-8-methoxy-4(1H)-quinolone (4.6 g, 0.017 mol) was heated under reflux in a mixture of phosphorus oxychloride (8 ml) and chloroform (50 ml) for 1.5 hours. When cool, the mixture was poured into a vigorously stirred mixture of sodium hydrogen carbonate solution, ice and chloroform. The layers were separated and the organic solution was washed with sodium hydrogen carbonate solution and brine. Evaporation of the chloroform solution afforded 4-chloro-3-hexanoyl-8-methoxyquinoline as a yellow-brown oil (5 g).

Workup

  1. temperatureWhen cool
  2. customThe layers were separated
  3. washthe organic solution was washed with sodium hydrogen carbonate solution and brine
  4. customEvaporation of the chloroform solution

Sources & evidence

ORD record
ord-8da8a9aae1a5466f9ef0b21dc5e3a0d4
Source dataset
uspto-grants-1989_02
Patent number
US04806550

Reaction notes

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