5-Nitro-3,3'-bipyridin-4-amine → [3,3'-Bipyridine]-4,5-diamine

HRID 2096946Notes

Reaction equation

HRID 2096946 reaction equation
[N+:1]([C:4]1[C:5]([NH2:16])=[C:6]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[N:8]1[CH:9]=[C:4]([NH2:1])[C:5]([NH2:16])=[C:6]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 581355295-Nitro-3,3'-bipyridin-4-amine

Product 1

HCID 46315401[3,3'-Bipyridine]-4,5-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-nitro-3,3′-bipyridin-4-amine (XLVII) (5 g, 23 mmol) in MeOH (20 mL) was added 10% Pd/C. The solution was purged with hydrogen and stirred at room temperature under hydrogen for 15 h. The suspension was filtered through Celite and the concentrated under vacuum to produce 3,3′-bipyridine-4,5-diamine (XLVIII) as off white solid (3.3 g, 17.7 mmol, 76% yield). 1H NMR (DMSO-d6, 400 MHz,): δ 8.63-8.53 (m, 1H), 7.90-7.83 (m, 1H), 7.75 (s, 1H), 7.58 (s, 1H), 7.48-7.43 (m, 2H), 6.13 (bs, 2H), 5.31 (bs, 2H). ESIMS found C10H10N4 m/z 187.10 (M+H).

Workup

  1. customThe solution was purged with hydrogen
  2. filtrationThe suspension was filtered through Celite
  3. concentrationthe concentrated under vacuum

Sources & evidence

ORD record
ord-d35b978f21c6489c8dc2c1bcbbc86092
Source dataset
uspto-grants-2013_05
Patent number
US08450340B2

Reaction notes

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