Ethanol → 1-Ethyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651400Notes

Reaction equation

HRID 1651400 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:26])=[C:10]([N:14]3[CH2:17][C:16]([CH3:25])([NH:18]C(=O)C(F)(F)F)[CH2:15]3)[C:11]=2[F:13])[C:6](=[O:27])[C:5]([C:28]([OH:30])=[O:29])=[CH:4]1)[CH3:2].[OH-].[Na+].C(O)C>O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:26])=[C:10]([N:14]3[CH2:15][C:16]([NH2:18])([CH3:25])[CH2:17]3)[C:11]=2[F:13])[C:6](=[O:27])[C:5]([C:28]([OH:30])=[O:29])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 117435771-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-3-quinolinecarboxylic acid

Product 1

HCID 117246061-Ethyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.65 g (1.5 mmoles) of 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-quinoline-3-carboxylic acid (example 21) 2 ml of 10% sodium hydroxide and 3 ml of ethanol is refluxed in 10 ml of water for 3 hours. It is filtered while hot, cooled, acidified with acetic acid, and filtered. After washing with water, 0.48 g (95%) of 1-ethyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 293°-6° C.

Workup

  1. filtrationIt is filtered while hot,
  2. temperaturecooled
  3. filtrationfiltered
  4. washAfter washing with water, 0.48 g (95%) of 1-ethyl-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  5. customare obtained

Sources & evidence

ORD record
ord-f824a9852bbc471caec994ac21b5bba4
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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