Acetic Acid → Diisopropyl Ether

HRID 1415934Notes

Reaction equation

HRID 1415934 reaction equation
[C:1](OC([NH:8][C:9]1[C:10]([F:34])=[C:11]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([F:27])=[C:23]([Cl:26])[N:24]=3)[C:19](=[O:28])[C:18]([C:29]([O:31]CC)=[O:30])=[CH:17]2)[CH:12]=[CH:13][C:14]=1[F:15])=O)(C)([CH3:3])[CH3:2].Cl.[C:36]([OH:39])(=O)[CH3:37].[CH:40](Cl)(Cl)Cl>O>[CH:1]([O:39][CH:36]([CH3:37])[CH3:40])([CH3:3])[CH3:2].[NH2:8][C:9]1[C:10]([F:34])=[C:11]([N:16]2[C:25]3[C:20](=[CH:21][C:22]([F:27])=[C:23]([Cl:26])[N:24]=3)[C:19](=[O:28])[C:18]([C:29]([OH:31])=[O:30])=[CH:17]2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6212ChloroformHCID 11005573HCID 11005573, compound

Product 2

HCID 7914Diisopropyl EtherHCID 11728361HCID 11728361, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Ethyl 1-(3-t-butoxycarbonylamino-2,4-difluorophenyl)-7-chloro-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (500 mg) was added to 8 ml of a mixture of 3N hydrochloric acid and acetic acid, which was stirred and heated at reflux for 3.5 hours. After 16 ml of distilled water was added, the reaction solution was heated at reflux for 10 minutes, then allowed to cool down, and combined with 80 ml of chloroform and 10 ml of distilled water. The solution was separated, the chloroform layer was concentrated in vacua. The precipitate was dispersed in ethanol, collected by filtration, and washed with ethanol and then with diisopropyl ether to give 295 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3.5 hours
  3. temperaturethe reaction solution was heated
  4. temperatureat reflux for 10 minutes
  5. temperatureto cool down
  6. customThe solution was separated
  7. concentrationthe chloroform layer was concentrated in vacua
  8. additionThe precipitate was dispersed in ethanol
  9. filtrationcollected by filtration
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-fe3c2ebfb65a42eaa4fc5fd64352bed3
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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