Benzene → 3-Methyl-6-(morpholin-4-yl)-1-benzofuran-2(3H)-one

HRID 544707Notes

Reaction equation

HRID 544707 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1C=CC=C[CH:3]=1.[NH2+:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.O.[CH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:3][CH:2]1[C:18]2[CH:19]=[CH:20][C:21]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:22][C:17]=2[O:9][C:1]1=[O:8]

Participants

4

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 7050142326021-56-7

Product 1

HCID 135769393-Methyl-6-(morpholin-4-yl)-1-benzofuran-2(3H)-one

Procedure

A mixture of 18.2 g (0.1 mole) of 4-methyl-3-(3-oxobutyl)-maleic acid anhydride and 22 g (0.105 mole) of morpholinium benzoate in 400 ml of benzene is heated under reflux for 48 hours using a water separator. The benzene is removed in vacuo, the residue is taken up in methylene chloride and the organic phase is extracted twice with saturated sodium bicarbonate solution. The crude product remaining after drying and after removal of the methylene chloride is chromatographed over silica gel with petroleum ether/ether. Pale-yellow crystals are obtained, which are recrystallised from methylene chloride/ether. In this manner 3-methyl-6-morpholino-benzofuran-2(3H)-one having a melting point of 118°-121° C. is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. customThe benzene is removed in vacuo
  4. extractionthe organic phase is extracted twice with saturated sodium bicarbonate solution
  5. customafter drying
  6. customafter removal of the methylene chloride
  7. customis chromatographed over silica gel with petroleum ether/ether
  8. customPale-yellow crystals are obtained
  9. customwhich are recrystallised from methylene chloride/ether

Sources & evidence

ORD record
ord-1504206789654178a7f5eab02af7e52f
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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