Pyridine → HCID 19862605, compound

HRID 1165168Notes

Reaction equation

HRID 1165168 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].[CH2:18]([N:20]([CH2:24][CH3:25])[C:21](Cl)=[O:22])[CH3:19].N1C=CC=CC=1>C(#N)C.C(Cl)Cl>[CH2:18]([N:20]([CH2:24][CH3:25])[C:21]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH3:16])[C:10]=1[CH3:17])=[O:22])[CH3:19]

Participants

7

Reactant 4

HCID 1049PyridineHCID 2972DeferiproneHCID 6916Diethylcarbamoyl chlorideHCID 8471Triethylamine

Product 1

HCID 19862605HCID 19862605, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

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 0.76 ml of diethylcarbamoyl chloride. The suspension still remains intact after 60 minutes and thin-layer chromatography shows that no reaction has taken place. Then 20 ml of pyridine are added to the mixture, which turns yellowish in colour. After a further 60 minutes the onset of reaction can be observed. This reaction is brought to completion by stirring for 16 hours. The volatile constituents are removed by evaporation under reduced pressure. The residue is dried under a high vacuum, then dissolved in methanol, and the solution is treated with activated carbon, filtered and concentrated by evaporation. The filtrate is taken up in 100 ml of ethyl acetate, whereupon a product crystallises. A furthher crystalline product can be obtained by working up the mother liquor. The two products are combined and dissolved in methylene chloride. The solution is washed twice with water and the organic phase is concentrated by evaporation. The residue is crystallised from ethyl acetate, affording 3-(diethylaminocarbonyloxy)-1,2-dimethyl-4(1H)-pyridinone with a melting point of 135°-137° C.

Workup

  1. customAfter a further 60 minutes the onset of reaction
  2. stirringby stirring for 16 hours
  3. customThe volatile constituents are removed by evaporation under reduced pressure
  4. customThe residue is dried under a high vacuum
  5. dissolutiondissolved in methanol
  6. additionthe solution is treated with activated carbon
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customcrystallises
  10. customA furthher crystalline product can be obtained
  11. washThe solution is washed twice with water
  12. concentrationthe organic phase is concentrated by evaporation
  13. customThe residue is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-cf8209f433d04aa6a24888d9863f7701
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

Loading…