Sodium Methoxide → Methyl 6-(phenylmethyl)-2-pyridinecarboximidate

HRID 2081579Notes

Reaction equation

HRID 2081579 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[N:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O-:17].[Na+]>CO>[CH2:1]([C:8]1[N:9]=[C:10]([C:14](=[NH:15])[O:17][CH3:16])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19780236HCID 19780236, compound

Product 1

HCID 53840049Methyl 6-(phenylmethyl)-2-pyridinecarboximidateYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

2-Benzyl-6-cyanopyridine (0.84 g, 0.0043 moles) was added to a solution of sodium methoxide in methanol [prepared by dissolving sodium metal (0.11 g, 0.0047 gram atoms) in methanol (10 ml)] and the mixture stirred at 20° C. for 5 hours. The methanol was evaporated, the residue taken up in chloroform and the precipitate filtered off through a silica bed. Removal of the solvent from the filtrate gave methyl 6-benzyl-2-picoline imidate (0.81 g, 84%) which was used in the next stage without further purification.

Workup

  1. customThe methanol was evaporated
  2. filtrationthe precipitate filtered off through a silica bed
  3. customRemoval of the solvent from the filtrate

Sources & evidence

ORD record
ord-d04b3f70527e45a288098794dae55943
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

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