N-(3-methylphenyl)-3-oxobutanamide → HCID 70633462, compound

HRID 597448Notes

Reaction equation

HRID 597448 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:13])[CH2:9][C:10]([CH3:12])=[O:11])[CH:2]=1.[CH:15]([O-])([O-])OC>C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:13])/[CH:9]=[C:10](\[O:11][CH3:15])/[CH3:12])[CH:2]=1

Participants

5

Reactant 2

HCID 296092N-(3-methylphenyl)-3-oxobutanamideHCID 53629101Methylorthoformate

Product 1

HCID 70633462HCID 70633462, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 80 g of N-(m-tolyl)-acetoacetamide, 80 g of methyl orthoformate, 100 ml of methanol and 1 g of p-toluene sulfonic acid was refluxed with stirring for 6 hours and the volatile material was distilled off under reduced pressure. 300 ml of toluene and 1.5 ml of quinoline were added and the mixture was heated to about 140° C for 3 hours and then the rest of the toluene was evaporated. The residue was chromatographed over silica gel with a mixture of 9-1 methylene chloride-ethyl acetate as eluant to obtain 40 g of N-(m-tolyl)-3-methoxy-crotonamide melting at 106° C.

Workup

  1. temperaturewas refluxed
  2. distillationthe volatile material was distilled off under reduced pressure
  3. addition300 ml of toluene and 1.5 ml of quinoline were added
  4. customthe rest of the toluene was evaporated
  5. customThe residue was chromatographed over silica gel with a mixture of 9-1 methylene chloride-ethyl acetate as eluant

Sources & evidence

ORD record
ord-e072640aa3fb470a8de254593e4d6786
Source dataset
uspto-grants-1977_03
Patent number
US04014679

Reaction notes

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