Ethanol → 2-([1,1'-Biphenyl]-4-yl)-6-fluoro-3-hydroxyquinoline-4-carboxylic acid

HRID 231653Notes

Reaction equation

HRID 231653 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=O)[C:5]2=[O:12].[OH-:13].[Na+].C(OCC([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=O)(=O)C.[CH2:34]([OH:36])[CH3:35]>O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([C:31]1[CH:32]=[CH:33][C:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:22]=3)=[CH:29][CH:30]=1)[C:5]([OH:12])=[C:35]2[C:34]([OH:13])=[O:36]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2365665-FluoroisatinHCID 20034058Acetic acid 2-biphenyl-2-yl-2-oxo-ethyl ester

Product 1

HCID 144981462-([1,1'-Biphenyl]-4-yl)-6-fluoro-3-hydroxyquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of 6.6 g of 5-fluoro-2,3-indolinedione in 48 ml of water was treated with a sufficient amount of a solution of 6.62 g of sodium hydroxide in 22 ml of water to provide solution. A warm solution of 10.17 g of acetoxyacetylbiphenyl in 80 ml of ethanol was added, followed by the balance of the alkali solution. The mixture was refluxed for 3 hours. During the last 1/2 hour 10 ml of ethanol was distilled off. A 103 ml portion of water was added, the mixture was stirred, cooled and filtered through diatomaceous earth. The filtrate was treated with 13.6 ml of concentrated hydrochloric acid and 4.39 ml of glacial acetic acid and stirred for 30 minutes. The resulting precipitate was collected, washed with water and ether and air dried. The resulting solid was stirred and heated in 400 ml of ethanol. The solid was collected, washed with water and dried giving 11.2 g of the desired product, mp 25220 -254° C.

Workup

  1. customto provide solution
  2. temperatureThe mixture was refluxed for 3 hours
  3. distillationDuring the last 1/2 hour 10 ml of ethanol was distilled off
  4. additionA 103 ml portion of water was added
  5. temperaturecooled
  6. filtrationfiltered through diatomaceous earth
  7. additionThe filtrate was treated with 13.6 ml of concentrated hydrochloric acid and 4.39 ml of glacial acetic acid
  8. stirringstirred for 30 minutes
  9. customThe resulting precipitate was collected
  10. washwashed with water and ether and air
  11. customdried
  12. stirringThe resulting solid was stirred
  13. temperatureheated in 400 ml of ethanol
  14. customThe solid was collected
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-6428a7d6028a46bf9d567d517a046ff6
Source dataset
uspto-grants-1989_07
Patent number
US04847381

Reaction notes

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