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

HRID 1071836Notes

Reaction equation

HRID 1071836 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>C(O)C>[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 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-methylaniline (1.07 g, 1.07 mL, 10.0 mmol), pyruvic acid (0.88 g, 0.70 mL, 10.0 mmol), and benzaldehyde (1.06 g, 1.01 mL, 10.0 mmol) in absolute ethanol (50 mL) was stirred at reflux for 3 h. After cooling, the solvent was removed in vacuo to give 3.52 g of a yellow paste, which was triturated with successive fresh portions of hexanes (3×100 mL). The solid was collected by filtration and airdried to yield the title compound (1.21 g) as a yellow-orange solid, which was used without further purification. MS (API+): M+1: 309 (100%).

Workup

  1. temperatureat reflux for 3 h
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. customto give 3.52 g of a yellow paste, which
  5. customwas triturated with successive fresh portions of hexanes (3×100 mL)
  6. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-3afb4881c00949ea9ff4b63c04a091e9
Source dataset
uspto-grants-2005_06
Patent number
US06906193B2

Reaction notes

Loading…