Morpholine → HCID 12944917, compound

HRID 1578280Notes

Reaction equation

HRID 1578280 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[CH:12]=[CH2:13])=[CH:4][C:3]=1[F:18].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CS(C)=O>[F:18][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)[N:9]([CH:12]=[CH2:13])[CH:8]=[C:7]([C:14]([OH:16])=[O:15])[C:6]2=[O:17]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12944918HCID 12944918, compound

Product 1

HCID 12944917HCID 12944917, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.6 g of 7-chloro-6-fluoro-4-oxo-1-vinyl-1,4-dihydro-quinoline-3-carboxylic acid, 3.5 cm 3 of morpholine and 30 cm3 of dimethylsulphoxide were heated for 15 hours under reflux. The solvent was removed by distillation under reduced pressure and the residue was taken up in 20 cm3 of ethanol. The insoluble solid was separated and recrystallised from 8 cm3 of a 1:1 (by volume) mixture of methylcellosolve and ethanol. 0.4 g of 6-fluoro-7-morpholino-4-oxo-1-vinyl-1,4-dihydroquinoline-3-carboxylic acid, m.p. 218°-220° C., was obtained.

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe insoluble solid was separated
  4. customrecrystallised from 8 cm3 of a 1:1 (by volume) mixture of methylcellosolve and ethanol

Sources & evidence

ORD record
ord-87b85e462c62415f80933687727de302
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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