Toluene → HCID 70633948, compound

HRID 259058Notes

Reaction equation

HRID 259058 reaction equation
[C:1]([O:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[NH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:21]1(C)C=CC(S(O)(=O)=O)=CC=1.N1C2C(=CC=CC=2)C=CC=1.C1(C)C=CC=CC=1>C([O-])([O-])OC>[C:1]([O:7][C:8]1[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=1)[NH:11][C:12](=[O:17])/[CH:13]=[C:14](\[O:16][CH3:21])/[CH3:15])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7047QuinolineHCID 21422767HCID 21422767, compound

Product 1

HCID 70633948HCID 70633948, compoundYield 2,955.3%

Reagents, catalysts & solvents 1

HCID 53629101MethylorthoformateSolvent

Conditions

Temperature
140 °C

Procedure

A solution of 47 g of m-valeryloxy-acetylacetanilide in 50 ml of methyl orthoformate and 0.5 g of p-toluene sulfonic acid stood at room temperature for 16 hours and then 1 g of quinoline and 200 ml of toluene were added thereto. The mixture was heated at 140°C. for 4 hours while removing the methanol formed and the solvent was then evaporated. The residue was chromatographed over silica gel and was eluted with an 8-2 methylene chloride-acetone mixture to obtain 25 g of m-valeryloxy-3-methoxy-crotonanilide (isomer E) melting at 84°C.

Workup

  1. customwhile removing the methanol
  2. customformed
  3. customthe solvent was then evaporated
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with an 8-2 methylene chloride-acetone mixture

Sources & evidence

ORD record
ord-751bdd2dfe1c45f6a5e4076fa8218586
Source dataset
uspto-grants-1977_07
Patent number
US04036633

Reaction notes

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