4-Hydroxybenzaldehyde → HCID 86754837, compound

HRID 1603750Notes

Reaction equation

HRID 1603750 reaction equation
CS([O:5][CH2:6][CH:7]1[CH2:11][N:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:9](=[O:20])[CH2:8]1)(=O)=O.O[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH2:11][CH:7]([CH2:6][O:5][C:22]3[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=3)[CH2:8][C:9]2=[O:20])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 3840273HCID 3840273, compound

Product 1

HCID 86754837HCID 86754837, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then, 3.20 g of {1-(4-methoxyphenyl)-2-pyrrolidon-4-yl}methyl methanesulfonate and 1.4 g of 4-hydroxybenzaldehyde were dissolved in 32 ml of anhydrous N,N-dimethylformamide, to which 1.92 g of anhydrous potassium carbonate were added. The resultant mixture was stirred at 70° C. for 15 hours. The reaction mixture was filtered and the filtrate was concentrated. The thus-obtained residue was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and then purified using gradient elution with hexane-ethyl acetate, whereby 2.86 g of the title compound were obtained (yield: 74%).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. extractionThe thus-obtained residue was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. custompurified
  10. washelution with hexane-ethyl acetate

Sources & evidence

ORD record
ord-ccfc9cb407734f219b3e8fd948de2b50
Source dataset
uspto-grants-1999_11
Patent number
US05990139

Reaction notes

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