Acetic Acid → Diisopropyl Ether

HRID 1415937

Reaction equation

HRID 1415937 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:27])[C:7]([C:22]([O:24]CC)=[O:23])=[CH:8][N:9]2[C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[C:15]([F:20])=[CH:14][C:13]=2[F:21])=[CH:4][C:3]=1[F:28].Cl.[C:30]([OH:33])(=O)[CH3:31].O.[CH2:35](O)C>>[CH:3]([O:33][CH:30]([CH3:31])[CH3:35])([CH3:4])[CH3:2].[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:27])[C:7]([C:22]([OH:24])=[O:23])=[CH:8][N:9]2[C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[C:15]([F:20])=[CH:14][C:13]=2[F:21])=[CH:4][C:3]=1[F:28]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 54102467Ethyl 7-chloro-1-(2,4-difluoro-5-methylaminophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Product 2

HCID 7914Diisopropyl EtherHCID 224410407-Chloro-1-(2,4-difluoro-5-methylaminophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid

Procedure

Ethyl 7-chloro-1-(2,4-difluoro-5-methylaminophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (150 mg) was added to 1 ml of a mixture of 3N hydrochloric acid and acetic acid (1/1, vol/vol), which was stirred and heated at reflux for 2 hours. After 5 ml of distilled water was added, the reaction solution was heated at reflux for a further 10 minutes and then allowed to cool down. The precipitate was dispersed in ethanol, collected by filtration, and washed with ethanol and then with diisopropyl ether to give 70 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperaturethe reaction solution was heated
  4. temperatureat reflux for a further 10 minutes
  5. temperatureto cool down
  6. filtrationcollected by filtration
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-b5f1180e84c64a09b1026431cbc4114a
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Linked notes

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