Ethylene Glycol → 4-(2-hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine-N-oxide

HRID 1586931Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([N+]([O-])=O)[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)[N+:9]=1[O-:10].[OH:21][CH2:22][CH2:23][OH:24]>>[OH:21][CH2:22][CH2:23][O:24][C:6]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)[N+:9]([O-:10])=[C:4]([CH3:3])[CH:5]=1

Participants

Reactant 3

HCID 174Ethylene Glycol

HCID 24758Sodium hydride

HCID 110321326,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide

Product 1

HCID 197601224-(2-hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine-N-oxide

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (2.07 g, 51.8 mmoles) was added to 1,2-dihydroxyethane (100 ml). After 15 minutes 6,6'-dimethyl-4-nitro-2,2'-bipyridine-N-oxide (17) (6.35 g, 25.9 mmoles) was added and the mixture was stirred at 60° C. for 4 hours. Excess of 1,2-dihydroxyethane was removed by evaporation in high vacuum and the product was purified by flash chromatography.

Workup

customExcess of 1,2-dihydroxyethane was removed by evaporation in high vacuum
customthe product was purified by flash chromatography

Sources & evidence

ORD record: ord-b8e02c553ef247bea26a3a872067728a
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05216134

Reaction notes

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