Hydrochloric Acid → 2-Oxo-4-phenyl-1,2-dihydroquinoline-3-carboxylic acid

HRID 726679Notes

Reaction equation

HRID 726679 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:22])[NH:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.C(O)C.[OH-].[K+].Cl>O>[C:16]1([C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7](=[O:22])[C:6]=2[C:4]([OH:5])=[O:3])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 151627361,2-Dihydro-4-phenyl-2-oxo-3-quinoline carboxylic acid ethyl ester

Product 1

HCID 151627412-Oxo-4-phenyl-1,2-dihydroquinoline-3-carboxylic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,2-dihydro-4-phenyl-2-oxo-3-quinoline carboxylic acid ethyl ester (5 g, 17 mmol), ethanol (20 ml), water (40 ml) and potassium hydroxide (5 g, 89 mmol) was refluxed with heat for 1.5 hours. To the reaction mixture was added 60 ml of 2N-HCl to acidify the mixture to obtain a precipitated crystal by filtration. The crystal obtained was recrystallized from ethanol to give 4.2 g (yield: 92.9%) of the title compound.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heat for 1.5 hours
  3. customto obtain a precipitated crystal
  4. filtrationby filtration
  5. customThe crystal obtained
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-4006e22df06341da8c02a8bdfb625527
Source dataset
uspto-grants-1998_01
Patent number
US05710162

Reaction notes

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