Dimethyl Sulfoxide → 6-Fluoro-1-methyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1578272Notes

Reaction equation

HRID 1578272 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].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.CS(C)=O>O>[F:17][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:22]1[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]1)[N:9]([CH3:12])[CH:8]=[C:7]([C:13]([OH:15])=[O:14])[C:6]2=[O:16]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 531671-MethylpiperazineHCID 127338791-Desmethyl-7-depyrazine-7-chloro Norfloxacin

Product 1

HCID 129449106-Fluoro-1-methyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acidYield 40.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.55 g (0.01 mol) of 7-chloro-6-fluoro-1-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 4.5 cm3 of 1-methylpiperazine (0.011 mol) and 32 cm3 of DMSO were heated at 110° C. for 4 hours. After cooling, the mixture was taken up in 150 cm3 of water. The crystalline precipitate was filtered off, washed and recrystallised from 100 cm3 of methylcellosolve. 1.3 g of 6-fluoro-1-methyl-7-(4-methylpiperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, m.p. 304° C. (decomposition), were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationThe crystalline precipitate was filtered off
  3. washwashed
  4. customrecrystallised from 100 cm3 of methylcellosolve

Sources & evidence

ORD record
ord-d55fd3d6ab2245c9b44286cad18b5d0d
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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