Acetic Acid → Methyl Picolinimidate

HRID 2231647Notes

Reaction equation

HRID 2231647 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5](C2C=CC=CC=2)[N:4]=1)#[N:2].[Na].[C:16](O)(=[O:18])C>C[O-].[Na+].CO>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1](=[NH:2])[O:18][CH3:16]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 27631452-CYANO-6-PHENYLPYRIDINEHCID 5360545Sodium

Product 1

HCID 152260Methyl Picolinimidate

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 10942334Sodium MethoxideSolvent

Procedure

2-Cyano-6-phenylpyridine (20 g) was dissolved in a solution of sodium methoxide in methanol prepared from methanol (200 ml) and metallic sodium (0.77 g). After the solution was left to stand overnight, acetic acid (2.0 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.

Workup

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

Sources & evidence

ORD record
ord-fba6e4b92bd14b80a52f23bc5405d076
Source dataset
uspto-grants-1988_11
Patent number
US04783466

Reaction notes

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