Benzyl Chloride → HCID 20568362, compound

HRID 1578277Notes

Reaction equation

HRID 1578277 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[F:18].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[CH2:25]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:18])=[C:2]([Cl:1])[CH:11]=2)[CH:6]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 3018009Ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 20568362HCID 20568362, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16.2 g of 7-chloro-3-ethoxycarbonyl-6-fluoro-4-hydroxyquinoline, 16.8 g of potassium carbonate and 150 cm3 of DMF were heated for one hour, whilst stirring, in a round-bottomed flask equipped with a reflux condenser. 27.5 cm3 of benzyl chloride were added and the heating and stirring were maintained until the pH of the medium was neutral, which required about 2 hours. The major part of the solvent was removed by distillation in vacuo (15 mm Hg) at 100° C. The residue was taken up in 300 cm3 of water. The mixture was extracted with 3×100 cm3 of chloroform. The combined organic extracts were washed with water, dried (MgSO4) and evaporated to dryness. The residue was recrystallised from methylcellosolve. 17.5 g (81%) of 1-benzyl-7-chloro-3-ethoxycarbonyl-6-fluoroquinoline, m.p. 211°-212° C., were obtained.

Workup

  1. customequipped with a reflux condenser
  2. stirringthe heating and stirring
  3. temperaturewere maintained until the pH of the medium
  4. customabout 2 hours
  5. customThe major part of the solvent was removed by distillation in vacuo (15 mm Hg) at 100° C
  6. extractionThe mixture was extracted with 3×100 cm3 of chloroform
  7. washThe combined organic extracts were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated to dryness
  10. customThe residue was recrystallised from methylcellosolve

Sources & evidence

ORD record
ord-7dbaf0a90cb94b50a447b4592d1935d2
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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