Glyoxal → 6'-Chloro-[2,3']bipyridinyl

HRID 1633749Notes

Reaction equation

HRID 1633749 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.O1[CH2:15][CH2:14]OC(O)C1O.[CH:18]([CH:20]=O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][CH:20]=[CH:18][N:9]=2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 7860GlyoxalHCID 961701,4-Dioxane-2,3-diolHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 109543616'-Chloro-[2,3']bipyridinylYield 82.5%

Procedure

The same synthesis procedures as in Example 1 were conducted except for using 2-chloro-5-cyanopyridine and 1,4-dioxane-2,3-diol in place of 4-cyanopyridine and a 40% glyoxal aqueous solution, respectively, and, after completion of the reaction, the organic layer was distilled under reduced pressure of 3.0 to 3.1 Torr to obtain a 150 to 152° C. fraction. Thus, there was obtained 151.0 g (yield: 82.5%) of the end product as pale yellow crystals. HPLC analysis revealed that purity of the product was 99.1%.

Workup

  1. customThe same synthesis procedures as in Example 1
  2. distillationthe organic layer was distilled under reduced pressure of 3.0 to 3.1 Torr
  3. customto obtain a 150 to 152° C. fraction

Sources & evidence

ORD record
ord-79bc5c527b104729a34ea806cfc73a4f
Source dataset
uspto-grants-2003_01
Patent number
US06504032B1

Reaction notes

Loading…