Sodium borohydride → [2,2'-Bipyridine]-4,4'-diamine

HRID 2222945Notes

Reaction equation

HRID 2222945 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[N+:12]([O-])=[CH:13][CH:14]=[C:15]([N+:17]([O-])=O)[CH:16]=2)[N+:7]([O-])=[CH:8][CH:9]=1)([O-])=O.[BH4-].[Na+]>CO.Cl.[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][N:7]=2)[CH:16]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 178526748HCID 178526748, compound

Product 1

HCID 191515[2,2'-Bipyridine]-4,4'-diamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1.34 g of 4,4′-dinitro-2,2′-bipyridine-1,1′-dioxide was suspended in 75 mL of methanol under argon. The mixture was cooled to 0° C. then 0.5 g of 5% Pd/C was added followed by portion wise addition of 1.82 g of sodium borohydride over 10 minutes. The mixture was allowed to warm to room temperature then stirred for 48 hours. The mixture was filtered through a two inch plug of Celite.® Rotary evaporation of the filtrate yielded an off-white solid that was dissolved in 100 mL of 20% HCl. Insoluble residue was removed by filtration then the solution was washed with 100 mL of ether followed by neutralization to pH=8 using 50% NaOH. Cooling to 4° C. yielded a white precipitate which was collected by filtration. The solid was dried under vacuum overnight to yield the desired product as a white powder.

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe mixture was filtered through a two inch plug of Celite
  3. custom® Rotary evaporation of the filtrate
  4. customyielded an off-white solid
  5. customInsoluble residue was removed by filtration
  6. washthe solution was washed with 100 mL of ether
  7. temperatureCooling to 4° C.
  8. customyielded a white precipitate which
  9. filtrationwas collected by filtration
  10. customThe solid was dried under vacuum overnight

Sources & evidence

ORD record
ord-77ea46eecb024ad582d679af32078684
Source dataset
uspto-grants-2008_05
Patent number
US07372609B2

Reaction notes

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