4-Methyl-5-nitro-2,3'-bipyridine → 4-Methyl-6-(pyridin-3-yl)pyridin-3-amine

HRID 1774950Notes

Reaction equation

HRID 1774950 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1.[H][H]>[Pd].CO>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 463160084-Methyl-5-nitro-2,3'-bipyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 463152564-Methyl-6-(pyridin-3-yl)pyridin-3-amineYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-methyl-5-nitro-2,3′-bipyridine (215 g, 1 mol), Pd/C (10 g, 10%) and MeOH (1000 mL) was stirred at room temperature for 16 h under 10 atm of hydrogen. After reaction, the mixture was filtered. The filtrate was evaporated at reduced pressure to afford 4-methyl-2,3′-bipyridin-5-amine as a yellow solid (152 g, 82%)

Workup

  1. customAfter reaction
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-e0ac3da9f5c349a2bf79d375b9dcf18f
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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