Toluene → HCID 68124295, compound

HRID 441278Notes

Reaction equation

HRID 441278 reaction equation
[CH:1]([O-])([O-])OC.[C:6]([NH:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[NH:16][C:17](=[O:22])[CH2:18][C:19](=[O:21])[CH3:20])(=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10].C1(C)C=CC=CC=1.N1C2C(=CC=CC=2)C=CC=1>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:6]([NH:12][C:13]1[CH:14]=[C:15]([CH:23]=[CH:24][CH:25]=1)[NH:16][C:17](=[O:22])/[CH:18]=[C:19](\[O:21][CH3:1])/[CH3:20])(=[O:11])[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7047QuinolineHCID 21419830HCID 21419830, compoundHCID 53629101Methylorthoformate

Product 1

HCID 68124295HCID 68124295, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

16.5 g of methyl orthoformate were added to a solution of 27.6 g of m-valeramido-acetylacetanilide in 50 ml of methanol and after the addition of 0.5 g of p-toluene sulfonic acid, the mixture was stirred for 72 hours at 20° C. 200 ml of toluene and 1 ml of quinoline were added and the mixture was heated at 140° C. for 1 hour while distilling a methanol-toluene azeotrope. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8- 2 methylene chloride-acetone mixture yielded 20 g of m-valeramido-3-methoxy-crotonanilide melting at 115° C. and after crystallization from ethyl acetate melted at 116° C.

Workup

  1. temperaturethe mixture was heated at 140° C. for 1 hour
  2. distillationwhile distilling a methanol-toluene azeotrope
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution with an 8- 2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-774bf5c3f37d4c8e856e32775a974227
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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