Acetic Acid → Methyl Picolinimidate

HRID 1651040Notes

Reaction equation

HRID 1651040 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][CH:3]=1.[Na].[C:11](O)(=[O:13])C>C[O-].[Na+].CO>[N:7]1[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=1[C:8](=[NH:9])[O:13][CH3:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5360545SodiumHCID 151008596-Bromopyridine-2-carbonitrile

Product 1

HCID 152260Methyl Picolinimidate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10942334Sodium MethoxideSolvent

Procedure

6-Bromo-2-cyano-pyridine (20 g) was dissolved in a solution of sodium methoxide in methanol prepared from methanol (300 ml) and metallic sodium (1.26 g). After the solution was left to stand for 15 minutes, acetic acid (3.3 g) was added thereto, followed by concentration under reduced pressure. The resulting residue was dissolved in ether (300 ml) and insoluble materials were filtered out. The filtrate was concentrated under reduced pressure to obtain methyl 2-picoline imidate derivative.

Workup

  1. waitAfter the solution was left
  2. concentrationfollowed by concentration under reduced pressure
  3. dissolutionThe resulting residue was dissolved in ether (300 ml)
  4. filtrationinsoluble materials were filtered out
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3a51f458a444d63af353df52a60cabf
Source dataset
uspto-grants-1990_05
Patent number
US04927827

Reaction notes

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