Hydrochloric Acid → HCID 22416539, compound

HRID 1720904Notes

Reaction equation

HRID 1720904 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1)#[N:2].Cl.N#[C:13][NH2:14]>C(O)CC>[C:13]([N:2]=[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1)[O:10][CH2:9][CH2:7][CH3:6])#[N:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 224165405-(Hydroxymethyl)nicotinonitrile

Product 1

HCID 22416539HCID 22416539, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

After 3-cyano-5-hydroxymethylpyridine (0.79 g, 5.9 mmol) was dissolved in 1-propanol (30 ml) and hydrogen chloride gas was passed into the solution under ice-cooling for 30 minutes, the reactor was tight sealed for stirring the mixture at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue was neutralized with a saturated aqueous sodium carbonate solution and extracted with chloroform (30 ml×3). The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in acetonitrile (20 ml), and an aqueous solution (30 ml) of cyanamide (0.50 g, 11.9 mmol), Na2HPO4 (0.84. g, 5.9 mmol) and NaH2PO4 ·2H2O (3.79 g, 23.7 mmol) was added to the solution. The mixture was stirred at room temperature for 10 hours. After the completion of the reaction, the mixture was extracted with chloroform (100 ml×3). The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product of propyl N-cyano-5-hydroxymethyl-3-pyridinecarboximidate.

Workup

  1. temperaturecooling for 30 minutes
  2. customthe reactor was tight sealed
  3. customAfter the completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. extractionextracted with chloroform (30 ml×3)
  6. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in acetonitrile (20 ml)
  9. stirringThe mixture was stirred at room temperature for 10 hours
  10. customAfter the completion of the reaction
  11. extractionthe mixture was extracted with chloroform (100 ml×3)
  12. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5301d63757143ebaa829632a2e5e75d
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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