Benzaldehyde → 6-methyl-2-phenylquinoline-4-carboxylic acid

HRID 1779362Notes

Reaction equation

HRID 1779362 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1.[C:17]([OH:22])(=[O:21])[C:18]([CH3:20])=O>C(O)C>[C:2]1([C:1]2[CH:20]=[C:18]([C:17]([OH:22])=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([CH3:16])[CH:14]=3)[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 1060Pyruvic AcidHCID 7813p-Toluidine

Product 1

HCID 6987076-methyl-2-phenylquinoline-4-carboxylic acidYield 9.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzaldehyde (2.12 g) and 2.14 g of p-toluidine were dissolved in 50 ml of ethanol, and 1.76 g of pyruvic acid were added thereto dropwise. The reaction mixture was then heat-refluxed for 6 hours. The resulting reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The residue was dissolved in a 1N sodium hydroxide aqueous solution. This aqueous solution was extracted with ethyl ether, and the aqueous layer was acidified with dilute hydrochloric acid. The precipitate was collected by filtration, and dried to form 0.51 g of the above-mentioned compound.

Workup

  1. temperatureThe reaction mixture was then heat-refluxed for 6 hours
  2. customThe resulting reaction mixture
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in a 1N sodium hydroxide aqueous solution
  5. extractionThis aqueous solution was extracted with ethyl ether
  6. filtrationThe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-dbaca45c3e8b4162aff69322deec4e26
Source dataset
uspto-grants-1997_05
Patent number
US05627193

Reaction notes

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