Malonic Acid → HCID 23360158, compound

HRID 2372333Notes

Reaction equation

HRID 2372333 reaction equation
[BH4-].[Na+].F[C:4](F)(F)[C:5]([OH:7])=[O:6].[C:10]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)#[N:11].C(O)(=O)CC(O)=O.N1CCCCC1>N1C=CC=CC=1.O1CCCC1.O1CCOCC1>[C:5](/[CH:4]=[CH:16]/[C:15]1[CH:18]=[CH:19][C:12]([CH2:10][NH2:11])=[CH:13][CH:14]=1)([OH:7])=[O:6]

Participants

9

Reactant 5

HCID 867Malonic AcidHCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 660424-CyanobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 23360158HCID 23360158, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

Into a mixture of 0.946 g of sodium borohydride and 100 ml of tetrahydrofuran, a mixed solution of 2.850 g of trifluoroacetic acid and 20 ml of tetrahydrofuran, was dropwise added under stirring and cooling with ice. After the completion of the dropwise addition, the ice bath was removed, and the reaction mixture was stirred for one hour. Then, a solution obtained by dissolving 4.325 g of 4-cyanociannamic acid obtained by heating and condensing 4-cyanobenzaldehyde with malonic acid in pyridine in the presence of a catalytic amount of piperidine, in 140 ml of tetrahydrofuran and 30 ml of 1,4-dioxane, was dropwise added to the reaction mixture, and stirred at room temperature for 2.5 hours. After cooling, ice pieces were added to decompose the excess reducing agent. Then, the reaction mixture was concentrated, and the precipitated powder was collected by filtration and subjected to vacuum drying to obtain 3.50 g of the above identified compound as a colorless powder.

Workup

  1. temperaturecooling with ice
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. stirringthe reaction mixture was stirred for one hour
  5. customThen, a solution obtained
  6. customobtained
  7. temperatureby heating
  8. stirringstirred at room temperature for 2.5 hours
  9. temperatureAfter cooling
  10. additionice pieces were added
  11. concentrationThen, the reaction mixture was concentrated
  12. filtrationthe precipitated powder was collected by filtration
  13. customdrying
  14. customto obtain 3.50 g of the

Sources & evidence

ORD record
ord-929d07e8022e4574adec8eedef52ab49
Source dataset
uspto-grants-1992_03
Patent number
US05098900

Reaction notes

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