Hydrochloric Acid → 4-(4-acetonylphenoxy)-3-hydroxy-1H-pyrrole-2,5-dione

HRID 465435Notes

Reaction equation

HRID 465435 reaction equation
[CH2:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH2:13])=[O:12])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[C:16](OCC)(=[O:22])[C:17](OCC)=[O:18].CC(C)([O-])C.[K+].Cl>CN(C)C=O.O>[CH2:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][C:10]2[C:11](=[O:12])[NH:13][C:17](=[O:18])[C:16]=2[OH:22])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 198745544-AcetonylphenoxyacetamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 547233674-(4-acetonylphenoxy)-3-hydroxy-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-acetonylphenoxyacetamide, ethylene ketal (3.2 g) and diethyl oxalate (2.0 g) in dry dimethylformamide at 0° C. was treated with potassium tert-butoxide (3.24 g) in two portions at 15 min. intervals. The solution was then stirred 16 h at ambient temperature, poured into water, and acidified with 6N hydrochloric acid. The aqueous solution was extracted with ethyl acetate, the combined organic extracts dried (magnesium sulphate), filtered and evaporated and the residue crystallised from acetone/ether to give 4-[4-acetonylphenoxy]-3-hydroxy-1H-pyrrole-2,5-dione, (1.5 g).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. dry with materialthe combined organic extracts dried (magnesium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue crystallised from acetone/ether

Sources & evidence

ORD record
ord-bda68225456c46d094d607f12db26774
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

Loading…