Acetic Acid → 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

HRID 1290895Notes

Reaction equation

HRID 1290895 reaction equation
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)([CH3:3])[CH3:2].[C:13](O)(=[O:18])[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:14]([C:15]([OH:17])=[O:16])[C:13]1=[O:18])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 110410352-((Propan-2-yl)amino)benzaldehyde

Product 1

HCID 109442901-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acidYield 55.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.0 g of 2-isopropylaminobenzaldehyde, 4.8 g of malonic acid, 5 ml of piperidine, 5 ml of acetic acid and 50 ml of toluene was heated to reflux for 3.5 hours. The reaction solution was washed with water. The crude product partly precipitated was filtered. The filtrate was extracted with 2N sodium hydroxide aqueous solution and the precipitates above was dissolved in the extract. The resulting solution was washed with toluene and aqueous hydrochloric acid solution was then added thereto to render the system acidic. The precipitates were washed with water and dried to give 3.9 g of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid.

Workup

  1. temperatureto reflux for 3.5 hours
  2. washThe reaction solution was washed with water
  3. customThe crude product partly precipitated
  4. filtrationwas filtered
  5. extractionThe filtrate was extracted with 2N sodium hydroxide aqueous solution
  6. customthe precipitates
  7. dissolutionabove was dissolved in the extract
  8. washThe resulting solution was washed with toluene and aqueous hydrochloric acid solution
  9. additionwas then added
  10. washThe precipitates were washed with water
  11. customdried

Sources & evidence

ORD record
ord-2e4904562eff4632b5045376396f0847
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Reaction notes

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