3-Quinolinecarboxylic acid, 7-amino-1-ethyl-6-fluoro-1,4-dihydro-4-oxo- → Irloxacin

HRID 1583549Notes

Reaction equation

HRID 1583549 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[NH2:12])[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18].CO[C:21]1(OC)[CH2:25][CH2:24][CH2:23]O1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH:21]=[CH:25][CH:24]=[CH:23]1)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18]

Participants

4

Reactant 2

HCID 6098843-Quinolinecarboxylic acid, 7-amino-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-HCID 11788317dimethoxytetrahydrofurane

Product 1

HCID 65828Irloxacin

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.5 Grams of 6-fluoro-7-amino-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are suspended in 15 ml of acetic acid, and 1.32 gram of dimethoxytetrahydrofuran is added; the mixture is heated gradually until the solid dissolves, and is then allowed to cool. The precipitate formed is filtered off and washed with ethanol. The product is recrystallized in acetonitrile, and 1.4 gram of needles is obtained, of melting point 251°-252° C.

Workup

  1. temperaturethe mixture is heated gradually until the solid
  2. dissolutiondissolves
  3. temperatureto cool
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with ethanol
  7. customThe product is recrystallized in acetonitrile

Sources & evidence

ORD record
ord-8d2cf8aa30364c9c9fe136f31303ad01
Source dataset
uspto-grants-1985_11
Patent number
US04552882

Reaction notes

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