1-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-(2-Chloromethylmorpholino)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 477855Notes

Reaction equation

HRID 477855 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[Cl:20][CH2:21][CH:22]1[O:27][CH2:26][CH2:25][NH:24][CH2:23]1>CS(C)=O>[Cl:20][CH2:21][CH:22]1[CH2:23][N:24]([C:10]2[C:11]([F:13])=[C:12]3[C:7]([C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4][N:3]3[CH2:1][CH3:2])=[CH:8][C:9]=2[F:15])[CH2:25][CH2:26][O:27]1

Participants

4

Reactant 2

HCID 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 102408592-(Chloromethyl)morpholine

Product 1

HCID 146526317-(2-Chloromethylmorpholino)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.54 g of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 0.60 g of 2-chloromethylmorpholine in 20 ml of dimethyl sulfoxide is stirred at 120° C. for 8 hours. The reaction mixture is concentrated under reduced pressure and to the residue is added water followed by extracting with chloroform. The organic layer is washed with water, dried over anhydrous magnesium sulfate and then the solvent is distilled off. Further, the obtained crystals are recrystallized from chloroform-methanol to give 7-(2-chloromethylmorpholino)-1-ethyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, melting at 212°-215° C.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure and to the residue
  2. additionis added water
  3. extractionby extracting with chloroform
  4. washThe organic layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off
  7. customFurther, the obtained crystals are recrystallized from chloroform-methanol

Sources & evidence

ORD record
ord-9d209b115b7941439a44b55ecd33dbfd
Source dataset
uspto-grants-1989_12
Patent number
US04889857

Reaction notes

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