Isatin → 3-Methyl-2-phenylquinoline-4-carboxylic acid

HRID 1779361Notes

Reaction equation

HRID 1779361 reaction equation
[OH-:1].[Na+].[NH:3]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=O)[C:4]1=[O:5].[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[CH2:15][CH3:16]>C(O)C>[C:18]1([C:14]2[C:15]([CH3:16])=[C:6]([C:4]([OH:1])=[O:5])[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 71481-Phenyl-1-propanoneHCID 14798Sodium Hydroxide

Product 1

HCID 6737103-Methyl-2-phenylquinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ten milliliters (2N) of a sodium hydroxide aqueous solution was added dropwise to an ethanol (20 ml) suspension containing 1.47 g of isatin and 2.68 g of propiophenone at room temperature, and the reaction mixture was then heat-refluxed for 26 hours. The resulting reaction mixture was allowed to cool, and then concentrated under reduced pressure. Ice water was added to the residue, and the mixture was extracted with ethyl ether. The aqueous layer was acidified with dilute hydrochloric acid. The precipitate was collected by filtration, and dried to form 1.47 g of the above-mentioned compound.

Workup

  1. temperaturethe reaction mixture was then heat-refluxed for 26 hours
  2. customThe resulting reaction mixture
  3. temperatureto cool
  4. concentrationconcentrated under reduced pressure
  5. additionIce water was added to the residue
  6. extractionthe mixture was extracted with ethyl ether
  7. filtrationThe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-c48241b95a1440dbad9e22b747187e48
Source dataset
uspto-grants-1997_05
Patent number
US05627193

Reaction notes

Loading…