Hydrochloric Acid → HCID 53780687, compound

HRID 1109370Notes

Reaction equation

HRID 1109370 reaction equation
C([O:8][NH:9][C:10]([N:12]1[CH2:16][CH2:15][C:14](=[CH:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([OH:26])=[C:20]([O:27][CH3:28])[CH:19]=2)[C:13]1=[O:29])=[O:11])C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1(OC)C=CC=CC=1.[N+](C)([O-])=O>[OH:8][NH:9][C:10]([N:12]1[CH2:16][CH2:15][C:14](=[CH:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([OH:26])=[C:20]([O:27][CH3:28])[CH:19]=2)[C:13]1=[O:29])=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 54560750HCID 54560750, compound

Product 1

HCID 53780687HCID 53780687, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6375NitromethaneSolventHCID 7519AnisoleSolvent2×

Procedure

To a solution of 800 mg (2 mmol) of 1-(N-benzyloxycarbamoyl)-3-(3,5-di-methoxy-4-hydroxybenzylidene)pyrrolidin-2-one in a mixture of anisole (12 ml) and nitromethane (12 ml) was added a solution of 1.6 g (12 mmol) of aluminium chloride in anisole (4 ml) under a nitrogen atmosphere while being stirred under ice-cooling and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 6 ml of cooled 2N hydrochloric acid and the mixture was stirred for 1 hour and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate and evaporated to give a residue, which was recrystallized from a methylene chloride/ether mixture to give 387 mg of the objective compound in 63% yield.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. stirringthe mixture was stirred for 1 hour
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a residue, which
  9. customwas recrystallized from a methylene chloride/ether mixture

Sources & evidence

ORD record
ord-c4df37d02082428786b4b86af57ed27f
Source dataset
uspto-grants-1994_06
Patent number
US05319099

Reaction notes

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