Sodium ethoxide → 6,6'-Dimethyl-4-ethoxy-2,2'-bipyridine-N-oxide

HRID 1586929Notes

Reaction equation

HRID 1586929 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+]([O-])=O)[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N+:7]=1[O-:8].[O-:19][CH2:20][CH3:21].[Na+].[Na]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][CH3:21])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[N+:7]=1[O-:8]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 110321326,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide

Product 1

HCID 149751976,6'-Dimethyl-4-ethoxy-2,2'-bipyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

6,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide (17) (1.0 g, 4.1 mmoles) was added to sodium ethoxide solution made from (0.19 g, 0.0083 g-atoms) sodium and 25 ml ethanol. The mixture was stirred at 70° C. for 30 minutes. After neutralization with concentrated hydrochloric acid the reaction mixture was filtered and evaporated to dryness. The product was purified by means of flash chromatography (silica, 0%-50% methanol/chloroform).

Workup

  1. filtrationAfter neutralization with concentrated hydrochloric acid the reaction mixture was filtered
  2. customevaporated to dryness
  3. customThe product was purified by means of flash chromatography (silica, 0%-50% methanol/chloroform)

Sources & evidence

ORD record
ord-0cbff4ab8b194c3c9fc006ad22ee3317
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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