p-Toluenesulfonic acid → HCID 70633993, compound

HRID 259062Notes

Reaction equation

HRID 259062 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[NH:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12])(=[O:3])[CH3:2].[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])OC.N1C2C(=CC=CC=2)C=CC=1>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:15]=[CH:16][CH:17]=1)[NH:8][C:9](=[O:14])/[CH:10]=[C:11](\[O:13][CH3:18])/[CH3:12])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7047QuinolineHCID 21422789HCID 21422789, compoundHCID 53629101Methylorthoformate

Product 1

HCID 70633993HCID 70633993, compoundYield 2,038%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 50 g of m-acetoxy-acetylacetanilide, 1 g of p-toluene sulfonic acid and 50 ml of methyl orthoformate was stirred for 16 hours at 20°C. and after the addition of 2 ml of quinoline and 200 ml of toluene, the reaction mixture was heated at 140°C. for 4 hours while distilling off a toluene-methanol azeotrope. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. The product was eluted with an 8-2 methylene chloride-acetone mixture and was crystallized from isopropyl ether to obtain 29.5 g of m-acetoxy-3-methoxy-crotonanilide melting at 111°C.

Workup

  1. temperaturethe reaction mixture was heated at 140°C. for 4 hours
  2. distillationwhile distilling off a toluene-methanol azeotrope
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washThe product was eluted with an 8-2 methylene chloride-acetone mixture
  6. customwas crystallized from isopropyl ether

Sources & evidence

ORD record
ord-3ce666a9f558444dacad639e2e4fea91
Source dataset
uspto-grants-1977_07
Patent number
US04036633

Reaction notes

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