N-(cyclopropylmethyl)-3-nitropyridin-2-amine → N2-(cyclopropylmethyl)pyridine-2,3-diamine

HRID 1913081Notes

Reaction equation

HRID 1913081 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 29766774N-(cyclopropylmethyl)-3-nitropyridin-2-amine

Product 1

HCID 28902457N2-(cyclopropylmethyl)pyridine-2,3-diamineYield 104.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3.5 g (18.1 mM) of N-(cyclopropylmethyl)-3-nitropyridin-2-amine in 36 ml of methanol, were added 700 mg of palladium on carbon at 5%. The reaction mixture was stirred for 3 h at room temperature under hydrogen atmosphere at room pressure. The catalyst was filtrated on Celite and the filtrate was evaporated under vacuum to give 3.1 g of N2-(cyclopropylmethyl)pyridine-2,3-diamine as a solid. Yield: 99.5%.

Workup

  1. filtrationThe catalyst was filtrated on Celite
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-d71a797399fc45ee9c3a3103acf68e67
Source dataset
uspto-grants-2013_12
Patent number
US08609689B2

Reaction notes

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