Ethyl Acetate → HCID 57025020, compound

HRID 1525124Notes

Reaction equation

HRID 1525124 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7](C(O)=O)=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.CC(=O)OCC>[OH-].[Na+]>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:18])[CH:7]=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 110551427-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 57025020HCID 57025020, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (2.0 g) was added portionwise to a boiling solution of Dowtherm (50 ml heated at 250° C.) and further stirred at this temperature for 1 h. The reaction mixture was allowed to reach rt and diluted with 1N NaOH (100 ml) and extracted with EA. The org. phase was discarded. The aq. phase was acidified with 3N HCl and extracted with ether/EA. The aq. layer was filtered and the filtrate was extracted with ether/EA. The combined org. layers were washed with water and brine dried over MgSO4, filtered and evaporated under reduced pressure affording a solid which was stirred in Hept/EA and filtered. The filtrate was concentrated under reduced pressure and purified by CC (EA to EA/MeOH 9:1), affording a beige solid.

Workup

  1. customto reach rt
  2. extractionextracted with EA
  3. extractionextracted with ether/EA
  4. filtrationThe aq. layer was filtered
  5. extractionthe filtrate was extracted with ether/EA
  6. washlayers were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customaffording a solid which
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. custompurified by CC (EA to EA/MeOH 9:1)
  14. customaffording a beige solid

Sources & evidence

ORD record
ord-fde659a1129a4844b9bc45e56959244e
Source dataset
uspto-grants-2015_07
Patent number
US09079922B2

Reaction notes

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