p-METHYLACETOPHENONE → 6-chloro-2-(4-methylphenyl)quinoline-4-carboxylic acid

HRID 638285Notes

Reaction equation

HRID 638285 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.[OH-:13].[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH3:23])=[CH:18][CH:17]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=1)[CH:23]=[C:5]2[C:6]([OH:11])=[O:13]

Participants

5

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 14798Sodium HydroxideHCID 872035-chloro-1H-indole-2,3-dione

Product 1

HCID 11330936-chloro-2-(4-methylphenyl)quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 18.15 g of 5-chloroisatin in 200 ml of ethanol was added 30 ml of 10N sodium hydroxide. To this mixture was added 16 ml (0.12 mol) of p-methylacetophenone, and it was stirred and heated under reflux for 3.2 hr. It was then concentrated in vacuo, and the residue was diluted to 250 ml with water. The above named acid was precipitated by the addition of acetic acid as a tan solid. Recrystallization from acetonitrile gave 31.6 g of the above-named acid as a tan solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3.2 hr
  3. concentrationIt was then concentrated in vacuo
  4. additionthe residue was diluted to 250 ml with water
  5. customwas precipitated by the addition of acetic acid as a tan solid
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-8679807a1c63495aa01dc9fcc46e342e
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

Loading…