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

HRID 1165167Notes

Reaction equation

HRID 1165167 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].[C:18](Cl)(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(#N)C.C(Cl)Cl>[C:18]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[C:10]=1[CH3:17])(=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 2972DeferiproneHCID 8124Octanoyl chlorideHCID 8471Triethylamine

Product 1

HCID 198625883-(n-octanoyloxy)-1,2-dimethyl-4-(1H)-pyridinone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

With stirring, 0.56 ml of triethylamine is added at room temperature to a suspension of 0.556 g of 3-hydroxy-1,2-dimethyl-4(1H)-pyridinone in 40 ml of acetonitrile and 40 ml of methylene chloride, followed by the addition of 1.02 ml of caprylyl chloride. A solution forms within 3 minutes and after 30 minutes the reaction is complete, and the volatile constituents are removed by evaporation under reduced pressure. The residue is dried under a high vacuum and crystallised from a mixture of methylene chloride and ethyl acetate. The 3-(n-octanoyloxy)-1,2-dimethyl-4-(1H)-pyridinone so obtained begins to sinter at 140° C. and decomposes at 180° C.

Workup

  1. waitafter 30 minutes the reaction is complete
  2. customthe volatile constituents are removed by evaporation under reduced pressure
  3. customThe residue is dried under a high vacuum
  4. customcrystallised from a mixture of methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-0b42757bf86e4eb58e5a4fb473db2d72
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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