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

HRID 2295800Notes

Reaction equation

HRID 2295800 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-bef5894dd2f04cb8add4d1e021654d30
Source dataset
uspto-grants-1984_01
Patent number
US04426380

Reaction notes

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