6-Cyclopropyl-3-nitropyridin-2-ol → 3-amino-6-propyl-2(1H)-Pyridinone

HRID 1378707

Reaction equation

HRID 1378707 reaction equation
[CH:1]1([C:4]2[NH:9][C:8](=[O:10])[C:7]([N+:11]([O-])=O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1>[Pd].C(OCC)(=O)C>[NH2:11][C:7]1[C:8](=[O:10])[NH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 220087796-Cyclopropyl-3-nitropyridin-2-ol

Product 1

HCID 212245473-amino-6-propyl-2(1H)-PyridinoneYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-cyclopropyl-3-nitro-2-(1H)-pyridinone (2 g, 13.3 mmol) and 10% palladium on carbon (600 mg) in ethyl acetate (100 ml) was stirred at room temperature under an atmosphere of hydrogen overnight. The catalyst was removed by filtration through a bed of Celite and the filtrate concentrated to yield 1.63 g of product as a white microcrystalline solid. 1H NMR (CDCl3) δ 0.94 (t, J=7.3 Hz, 3 H), 1.67 (m, 2 H), 2.49 (t, J=7.5 Hz, 2 H), 4.00 (br s), 5.88 (d, J=7.1 Hz, 1 H), 6.59 (d, J=7.1 Hz, 1 H).

Workup

  1. customThe catalyst was removed by filtration through a bed of Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-7403dd075ce54a5db2372e17771243d7
Source dataset
uspto-grants-1997_09
Patent number
US05668289

Linked notes

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