Benzaldehyde → 8-methyl-2-phenylquinoline-4-carboxylic acid

HRID 1199938Notes

Reaction equation

HRID 1199938 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]([OH:14])(=[O:13])[C:10]([CH3:12])=O.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCO>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:12]=[C:10]2[C:9]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 1060Pyruvic AcidHCID 7242O-Toluidine

Product 1

HCID 7459528-methyl-2-phenylquinoline-4-carboxylic acidYield 19.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2 -methylaniline (28 g) in EtOH (50 mL) was added to a solution of pyruvic acid (33 g) and benzaldehyde (28 g) in EtOH (100 mL), and the mixture was heated under reflux for 3 h and then allowed to cool overnight. The resulting solid was collected by filtration, washed well with cold EtOH and benzene and dried to give a product (13.4 g) of acceptable purity. A sample crystallized from EtOH had mp 245°-246° C. (lit. mp 245° C. Doebner and Giesecke, Ann. 1887, 242, 290).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h
  3. temperatureto cool overnight
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed well with cold EtOH and benzene
  6. customdried

Sources & evidence

ORD record
ord-37b00917c172472aaabe031168569509
Source dataset
uspto-grants-1990_02
Patent number
US04904659

Reaction notes

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