Deferiprone → 3-Ethoxycarbonyloxy-1,2-dimethyl-4(1H)-pyridinone

HRID 1165166Notes

Reaction equation

HRID 1165166 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[C:10]=1[CH3:17].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(#N)C.C(Cl)Cl>[CH2:22]([O:21][C:19]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[C:10]=1[CH3:17])=[O:20])[CH3:23]

Participants

6

Reactant 3

HCID 2972DeferiproneHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 198625943-Ethoxycarbonyloxy-1,2-dimethyl-4(1H)-pyridinone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

With stirring, 11.2 ml of triethylamine are added at room temperature to a suspension of 5.56 g of 3-hydroxy-1,2-dimethyl-4(1H)-pyridinone in 100 ml of acetonitrile and 100 ml of methylene chloride, followed by the addition of 7.64 ml of ethyl chloroformate. Within 15 minutes a complete solution forms and, after a further 45 minutes, the volatile constituents are removed by evaporation under reduced pressure. The residue is dried under a high vacuum and the unreacted starting material is crystallised from ethyl acetate. 3-Ethoxycarbonyloxy-1,2-dimethyl-4(1H)-pyridinone is obtained from the mother liquor in the form of a yellow foam with a melting point of 113°-115° C.; thin-layer chromatogram: Rf=0.05 (7:3 mixture of methylene chloride and acetone), 0.10 (9:1 mixture of methylene chloride and isopropanol, 0.20 (9:1 mixture of methylene chloride and methanol), and 0.35 (4:1 mixture of methylene chloride and methanol).

Workup

  1. waitafter a further 45 minutes
  2. customthe volatile constituents are removed by evaporation under reduced pressure
  3. customThe residue is dried under a high vacuum
  4. customis crystallised from ethyl acetate

Sources & evidence

ORD record
ord-fa7da7841b0847648999ce816fc87180
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

Loading…