N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amine → N3-ethylpyridine-3,4-diamine

HRID 895671Notes

Reaction equation

HRID 895671 reaction equation
[CH2:1]([NH:3][C:4]1[CH:5]=[N+:6]([O-])[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH3:2]>CO.[Pd]>[CH2:1]([NH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH2:10])[CH3:2]

Participants

4

Reactant 1

HCID 12343672N-Ethyl-4-nitro-1-oxo-1lambda~5~-pyridin-3-amine

Product 1

HCID 11550019N3-ethylpyridine-3,4-diamineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-ethylamino-4-nitro-pyridine 1-oxide (1.5 g, 8.19 mmol), in methanol (30 mL) is hydrogenated over 10% Pd—C (1.5 g) at 50-60 psi for 48 hours. The catalyst is removed by filtration through a pad of celite, and the solvent is evaporated under vacuum to afford N3-Ethyl-pyridine-3,4-diamine as an white solid (1 g); 1H NMR (300 MHz, CDCl3): δ 7.59 (s, 1H), 7.57 (d, J=2.4 Hz, 1H), 6.56 (d, J=5.4 Hz, 1H), 3.20 (t, J=7.2 Hz, 2H), 1.29 (t, J=7.2 Hz, 3H), m/z 138 [M+1].

Workup

  1. customThe catalyst is removed by filtration through a pad of celite
  2. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-d4facde89a12441e9da3a30da1424748
Source dataset
uspto-grants-2005_07
Patent number
US06916827B2

Reaction notes

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