Sodium Methoxide → HCID 53896835, compound

HRID 2081588Notes

Reaction equation

HRID 2081588 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]#[N:12])[N:6]=1.[CH3:17][O-:18].[Na+]>CO>[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][C:5]1[N:6]=[C:7]([C:11](=[NH:12])[O:18][CH3:17])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19780237HCID 19780237, compound

Product 1

HCID 53896835HCID 53896835, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

2-(o-Chlorobenzyl)-6-cyanopyridine (5.0 g, 0.022 moles) was added to a solution of sodium methoxide in methanol [prepared by dissolving sodium metal (0.55 g, 0.024 g atoms) in methanol (50 ml)] and the mixture stirred at 20° C. for 5 hours. The methanol was evaporated, the residue taken up in dichloromethane and the precipitate filtered off through a silica bed. Removal of the solvent from the filtrate gave methyl 6-(o-chlorobenzyl)-2-picoline imidate (5.5 g, 100%) as a brown oil 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-cf43e46118544e008f26b14f6fc1aa57
Source dataset
uspto-grants-1993_02
Patent number
US05185339

Reaction notes

Loading…