Ethanol → HCID 10319998, compound

HRID 1651408Notes

Reaction equation

HRID 1651408 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:32])=[C:16]([N:20]3[CH2:23][C:22]([CH3:31])([NH:24]C(=O)C(F)(F)F)[CH2:21]3)[C:17]=2[F:19])[C:12](=[O:33])[C:11]([C:34]([OH:36])=[O:35])=[CH:10]1.[OH-].[Na+].C(O)C>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:32])=[C:16]([N:20]3[CH2:23][C:22]([NH2:24])([CH3:31])[CH2:21]3)[C:17]=2[F:19])[C:12](=[O:33])[C:11]([C:34]([OH:36])=[O:35])=[CH:10]1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 10459230HCID 10459230, compound

Product 1

HCID 10319998HCID 10319998, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.1 g (2.1 mmoles) of 1-(2,4-difluorophenyl)-6,8-difluoro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (example 34), 4 ml of 10% sodium hydroxide, 5 ml of ethanol and 25 ml of water is heated under reflux for 3 hours. It is cooled, filtered, acetic acid is added and the product filtered and washed with water and cold ethanol. 0.2 g (22%) of 1-(2,4-difluorophenyl)-6,8-difluoro-7-(3-amino-3-methyl-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid are obtained, melting at 185°-6° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureIt is cooled
  3. filtrationfiltered
  4. additionacetic acid is added
  5. filtrationthe product filtered
  6. washwashed with water and cold ethanol

Sources & evidence

ORD record
ord-4e329d0158474704829a3f1c190fe9b0
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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