Sodium borohydride → 4-Amino-6,6'-dimethyl-2,2'-bipyridine

HRID 1586928Notes

Reaction equation

HRID 1586928 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:16]([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-].[BH4-].[Na+]>CO.[Pd]>[NH2:16][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 110321326,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide

Product 1

HCID 197601464-Amino-6,6'-dimethyl-2,2'-bipyridineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6,6'-Dimethyl-4-nitro-2,2'-bipyridine-N-oxide (17) (2.0 g, 8.2 mmoles) was dissolved in methanol (20 ml). 10% palladium on carbon (0.36 g) was added followed by slow addition of sodium borohydride (3.6 g, 95 mmoles). After one hour the reaction mixture was filtered and the solution was evaporated. The residue was dissolved in 0.1N sodium hydroxide solution and the product was extracted with chloroform from the water phase. The chloroform phase was dried and evaporated. Yield: 80%

Workup

  1. filtrationAfter one hour the reaction mixture was filtered
  2. customthe solution was evaporated
  3. dissolutionThe residue was dissolved in 0.1N sodium hydroxide solution
  4. extractionthe product was extracted with chloroform from the water phase
  5. dry with materialThe chloroform phase was dried
  6. customevaporated

Sources & evidence

ORD record
ord-4d57c6ee2b8449659bd38058f53038b3
Source dataset
uspto-grants-1993_06
Patent number
US05216134

Reaction notes

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