Sodium borohydride → 4-(2-Hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine

HRID 1586932Notes

Reaction equation

HRID 1586932 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[N+:8]([O-])=[C:9]([CH3:11])[CH:10]=1.[BH4-].[Na+]>CO.[Pd]>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 197601224-(2-hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine-N-oxide

Product 1

HCID 197601174-(2-Hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2-hydroxyethoxy)-6,6'-dimethyl-2,2'-bipyridine-N-oxide (23) (2.40 g, 9.22 mmoles) was dissolved in methanol (75 ml). 10% palladium on carbon (0.54 g) was added and then slowly sodium borohydride (3.24 g, 85.6 mmoles). Palladium on carbon was filtered out and the solvent was evaporated. The product was purified by means of flash chromatography (silica, 5-50% methanol/chloroform).

Workup

  1. filtrationPalladium on carbon was filtered out
  2. customthe solvent was evaporated
  3. customThe product was purified by means of flash chromatography (silica, 5-50% methanol/chloroform)

Sources & evidence

ORD record
ord-50da65f52c124b6ea43302440c8aaecf
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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