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

HRID 1165177Notes

Reaction equation

HRID 1165177 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].[CH3:18][C:19]([CH3:24])([CH3:23])[C:20](Cl)=[O:21]>C(Cl)Cl.C(#N)C>[CH3:16][N:11]1[CH:12]=[CH:13][C:14](=[O:15])[C:9]([O:8][C:20](=[O:21])[C:19]([CH3:24])([CH3:23])[CH3:18])=[C:10]1[CH3:17]

Participants

6

Reactant 3

HCID 2972DeferiproneHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 198625981,2-dimethyl-3-pivaloyloxy-4(1H)-pyridinone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

5.6 ml of triethylamine are added to a suspension of 5.56 g of 3-hydroxy-1,2-dimethyl-4(1H)-pyridinone in 400 ml of methylene chloride and 400 ml of acetonitrile, followed by the addition, over 30 minutes, of 7.38 ml of trimethylacetyl chloride. The reaction is complete after 15 minutes. The resultant solution is concentrated by evaporation under reduced pressure, the residue is taken up in water and extracted with methylene chloride. The residue of the organic extract is crystallised from 500 ml of ethyl acetate, affording 1,2-dimethyl-3-pivaloyloxy-4(1H)-pyridinone, which melts at 112°-113° C. (sinters from 103° C.).

Workup

  1. concentrationThe resultant solution is concentrated by evaporation under reduced pressure
  2. extractionextracted with methylene chloride
  3. extractionThe residue of the organic extract
  4. customis crystallised from 500 ml of ethyl acetate

Sources & evidence

ORD record
ord-47a7402f661f49de8854024f861fdb98
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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