Acetic Acid → HCID 10329892, compound

HRID 1720899Notes

Reaction equation

HRID 1720899 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1)#[N:2].[CH3:10][O-].[Na+].[C:13]([OH:16])(=O)[CH3:14]>C(O)CC>[CH3:9][C:7]1[CH:8]=[C:3]([C:1](=[NH:2])[O:16][CH2:13][CH2:14][CH3:10])[CH:4]=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6378385-MethylnicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 10329892HCID 10329892, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Cyano-5-methylpyridine (2 g, 16.9 mmol) was dissolved in 1-propanol (100 ml). Sodium methoxide (46 mg, 0.85 mmol) was added, and the resulting mixture was stirred at 0° C. for 20 hours. After the completion of the reaction, the reaction mixture was neutralized with acetic acid (56 mg, 0.93 mmol), and the resulting mixture was concentrated under reduced pressure. After concentration, ethyl ether (50 ml) was added to the residue, and insoluble sodium acetate was removed by filtration. The filtrate was concentrated under reduced pressure to give a crude product of propyl 5-methyl-3-pyridinecarboximidate.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. concentrationAfter concentration, ethyl ether (50 ml)
  4. additionwas added to the residue, and insoluble sodium acetate
  5. customwas removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dcae75bf85fb48e7928c6560b9a4e6b8
Source dataset
uspto-grants-1996_04
Patent number
US05508293

Reaction notes

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