Quinoline → HCID 68125247, compound

HRID 441273Notes

Reaction equation

HRID 441273 reaction equation
[CH:1]([O-])([O-])OC.[C:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[NH:13][C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])(=[O:8])[CH3:7].N1C2C(=CC=CC=2)C=CC=1>CO>[C:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=1)[NH:13][C:14](=[O:19])/[CH:15]=[C:16](\[O:18][CH3:1])/[CH3:17])(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 21419824HCID 21419824, compoundHCID 53629101Methylorthoformate

Product 1

HCID 68125247HCID 68125247, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

11.7 g of methyl orthoformate were added to a solution of 23.4 g of m-acetamido-acetylacetanilide in 250 ml of anhydrous methanol and the mixture was refluxed for 3 hours and cooled. 0.6 ml of quinoline were added thereto and the methanol was distilled off under reduced pressure. Toluene was added to the residue and the mixture was heated at 140° C. for one hour while distilling a methanol-toluene azeotrope. The mixture was then concentrated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with ethyl acetate yielded 14.5 g of m-acetamido-3-methoxy-crotonanilide melting at 167° C. Crystallization from acetone did not change the melting point.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperaturecooled
  3. distillationthe methanol was distilled off under reduced pressure
  4. additionToluene was added to the residue
  5. distillationwhile distilling a methanol-toluene azeotrope
  6. concentrationThe mixture was then concentrated to dryness under reduced pressure
  7. customthe residue was chromatographed over silica gel
  8. washElution with ethyl acetate

Sources & evidence

ORD record
ord-2c46b7b8524d41cb8729585649132d93
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

Loading…