Hydrazine → N~2~-Ethylpyridine-2,3-diamine

HRID 333550Notes

Reaction equation

HRID 333550 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2].NN>C(O)C.[Pd]>[CH2:1]([NH:3][C:4]1[C:9]([NH2:10])=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 120157272-Ethylamino-3-nitropyridine

Product 1

HCID 13451717N~2~-Ethylpyridine-2,3-diamineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

N-ethyl-3-nitropyridin-2-amine (19.50 g, 117 mmol) was dissolved in 200 mL of ethanol at room temperature with suspended palladium on carbon 10% (1 g, 9.40 mmol). A solution of hydrazine (14.95 g, 467 mmol) in 50 mL of ethanol was added dropwise at room temperature, and reaction was stirred overnight. Filtering through Celite® pad and evaporation provided N2-ethylpyridine-2,3-diamine as a dark red solid (12 g, 75%).

Workup

  1. customreaction
  2. filtrationFiltering through Celite® pad and evaporation

Sources & evidence

ORD record
ord-f6248baa54af481fb04faaaf68589dac
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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