Morpholine → 6-Fluoro-1-methyl-7-(morpholin-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1578273Notes

Reaction equation

HRID 1578273 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:16])[C:7]([C:13]([OH:15])=[O:14])=[CH:8][N:9]2[CH3:12])=[CH:4][C:3]=1[F:17].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CS(C)=O>[F:17][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:9]([CH3:12])[CH:8]=[C:7]([C:13]([OH:15])=[O:14])[C:6]2=[O:16]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 127338791-Desmethyl-7-depyrazine-7-chloro Norfloxacin

Product 1

HCID 129449116-Fluoro-1-methyl-7-(morpholin-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.55 (0.01 mol) of 7-chloro-6-fluoro-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 3.5 cm3 of morpholine (0.01 mol) and 34 cm3 of DMSO were heated at 110° C. for 7 hours, whilst stirring. The reaction product precipitated after heating for 5 hours. After cooling, the mixture was diluted with water (100 cm3) and the solid was filtered off, washed with water and recrystallised from DMF (45 cm3). 1 g of 6-fluoro-1-methyl-7-morpholino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 316° C. (decomposition), was obtained.

Workup

  1. customThe reaction product precipitated
  2. temperatureafter heating for 5 hours
  3. temperatureAfter cooling
  4. additionthe mixture was diluted with water (100 cm3)
  5. filtrationthe solid was filtered off
  6. washwashed with water
  7. customrecrystallised from DMF (45 cm3)

Sources & evidence

ORD record
ord-d0e1849b5a2e4f5d8eeafe6578e4fe9a
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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