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

HRID 1651398Notes

Reaction equation

HRID 1651398 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:31])=[C:15]([N:19]4[CH2:22][C:21]([CH3:30])([NH:23]C(=O)C(F)(F)F)[CH2:20]4)[C:16]=3[F:18])[C:11](=[O:32])[C:10]([C:33]([OH:35])=[O:34])=[CH:9]2)=[CH:4][CH:3]=1.O>[OH-].[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:31])=[C:15]([N:19]4[CH2:22][C:21]([NH2:23])([CH3:30])[CH2:20]4)[C:16]=3[F:18])[C:11](=[O:32])[C:10]([C:33]([OH:35])=[O:34])=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 962WaterHCID 100746561-(4-Fluorophenyl)-6,8-difluoro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 103637901-(4-Fluorophenyl)-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1.25 g (2.5 mmoles) of 1-(4-fluorophenyl)-6,8-difluoro-7-(3-amino-3-trifluoroacetamido-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (example 19), in 8 ml of 1N sodium hydroxide and 10 ml of water is heated under reflux for 3 hours. It is cooled, filtered, and acetic acid is added. After filtering and washing with water and cold ethanol, 0.8 g (72%) of 1-(4-fluorophenyl)-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 272°-7° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. additionacetic acid is added
  5. filtrationAfter filtering
  6. washwashing with water and cold ethanol, 0.8 g (72%) of 1-(4-fluorophenyl)-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  7. customare obtained

Sources & evidence

ORD record
ord-42c4bff62c244bf9a1ded44658a99172
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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