4-amino-1-ethyl-3-nitro-1H-pyridin-2-one → 3,4-diamino-1-ethyl-1H-pyridin-2-one

HRID 1376218Notes

Reaction equation

HRID 1376218 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:8][CH3:9])[C:4](=[O:10])[C:3]=1[N+:11]([O-])=O>[Pd].CCO.C1COCC1>[NH2:11][C:3]1[C:4](=[O:10])[N:5]([CH2:8][CH3:9])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

4

Reactant 1

HCID 714223344-amino-1-ethyl-3-nitro-1H-pyridin-2-one

Product 1

HCID 451166373,4-diamino-1-ethyl-1H-pyridin-2-oneYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of 4-amino-1-ethyl-3-nitro-1H-pyridin-2-one (0.94 g, 5.13 mmol) in 1:3 EtOH/THF (20 mL) was hydrogenated over 10% Pd/C (0.55 g, 0.51 mmol) at room temperature. After 1 h, the catalyst was removed by filtration, rinsing with MeOH. The filtrate was concentrated to provide 3,4-diamino-1-ethyl-1H-pyridin-2-one (0.75 g, 95% yield). 1H-NMR (DMSO): δ 6.87 (d, 1H, J=7.2 Hz), 5.76 (d, 1H, J=7.6 Hz), 5.10 (m, 2H), 3.87 (m, 2H), 3.79 (q, 2H, J=7.2 Hz), 1.14 (t, 3H, J=7.2 Hz). MS: calculated for C7H11N3O+H 154.1; found: 154.2.

Workup

  1. customthe catalyst was removed by filtration
  2. washrinsing with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c28b25dea1484f04b4a2d727e075fe83
Source dataset
uspto-grants-2007_01
Patent number
US07169926B1

Reaction notes

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