Ethanol → 3-Hydroxy-6-methyl-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

HRID 231650

Reaction equation

HRID 231650 reaction equation
[CH3:1][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>[OH:12][C:5]1[C:6]([C:26]2[CH:25]=[CH:24][C:23]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:22][CH:27]=2)=[N:7][C:8]2[C:4]([C:35]=1[C:34]([OH:13])=[O:36])=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=2

Participants

6

Reactant 4

HCID 702EthanolHCID 118405-MethylisatinHCID 14798Sodium HydroxideHCID 20034058Acetic acid 2-biphenyl-2-yl-2-oxo-ethyl ester

Product 1

HCID 144981453-Hydroxy-6-methyl-2-[1,1'-biphenyl]-4-yl-4-quinolinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 30 g of 5-methyl-2,3-indolinedione in 200 ml of water and 30.6 g of sodium hydroxide in 100 ml of water was reacted with a solution of 47.4 g of acetoxyacetylbiphenyl in 500 ml of ethanol. The mixture was refluxed for 3 hours, then 250 ml of ethanol was removed by distillation. A 500 ml portion of water was added, The mixture was stirred, cooled to room temperature and filtered through diatomaceous earth. The filtrate was acidified with 60 ml of concentrated hydrochloric acid and 20 ml of glacial acetic acid. The resulting solid was collected, taken up in dilute ammonia and the insoluble portion collected. This solid was dissolved in 7.4N ammonia, filtered and precipitated with glacial acetic acid, giving 32.0 g of the desired product, mp 236°-238° C.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. custom250 ml of ethanol was removed by distillation
  3. additionA 500 ml portion of water was added
  4. filtrationfiltered through diatomaceous earth
  5. customThe resulting solid was collected
  6. customthe insoluble portion collected
  7. dissolutionThis solid was dissolved in 7.4N ammonia
  8. filtrationfiltered
  9. customprecipitated with glacial acetic acid

Sources & evidence

ORD record
ord-17d4ac50c57b4598a3bd803118256f0b
Source dataset
uspto-grants-1989_07
Patent number
US04847381

Linked notes

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