Sodium Methoxide → HCID 53884800, compound

HRID 2081583Notes

Reaction equation

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

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 53763119HCID 53763119, compound

Product 1

HCID 53884800HCID 53884800, compoundYield 130.9%

Conditions

Temperature: 20 °C

Procedure

2-p-Chlorobenzyl-6-cyanopyridine (1.69 g, 0.0074 moles) was added to a solution of sodium methoxide [prepared by dissolving sodium metal (0.19 g, 0.0081 gram atoms) in methanol (20 ml)] under nitrogen, and the mixture stirred at 20° C. for 17 hours. The methanol was evaporated, the residue taken up in chloroform, neutralised with acetic acid and the precipitate filtered off on HYFLO. Concentration of the filtrate gave methyl 6-p-chlorobenzyl-2-picoline imidate (1.20 g, 62%) which was used in the next stage without further purification.

Workup

customThe methanol was evaporated
filtrationthe precipitate filtered off on HYFLO

Sources & evidence

ORD record: ord-32dadcce765d4e4b84d4f5603c2be7b6
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05185339

Reaction notes

Loading…