Acetic Acid → Methyl Picolinimidate

HRID 1607874Notes

Reaction equation

HRID 1607874 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5](CCC)[N:4]=1)#[N:2].[Na].[C:13](O)(=[O:15])C>C[O-].[Na+].CO>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1](=[NH:2])[O:15][CH3:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 143034236-Propylpicolinonitrile

Product 1

HCID 152260Methyl PicolinimidateYield 618.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10942334Sodium MethoxideSolvent

Procedure

2-Cyano-6-n-propylpyridine (10 g) was dissolved in a solution of sodium methoxide in methanol prepared from methanol (100 ml) and metallic sodium (0.32 g). After standing overnight, acetic acid (0.82 g) was added thereto, followed by concentration under reduced pressure. The resulting residue was dissolved in ether (200 ml) and insoluble materials were filtered out. The filtrate was concentrated under reduced pressure to obtain methyl 2-picoline-imidate (11.5 g, yield: 94%).

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ether (200 ml)
  3. filtrationinsoluble materials were filtered out
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3dc1dee8698c490a9b85e1b12eb424a4
Source dataset
uspto-grants-1989_09
Patent number
US04868178

Reaction notes

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