1,3-dimethyl-5-nitropyridin-2(1H)-one → 5-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

HRID 2204426Notes

Reaction equation

HRID 2204426 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]1=[O:12]>CO.C1COCC1.[Pd]>[NH2:8][C:6]1[CH:5]=[C:4]([CH3:11])[C:3](=[O:12])[N:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 1

HCID 46575261,3-dimethyl-5-nitropyridin-2(1H)-one

Product 1

HCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-oneYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,3-dimethyl-5-nitropyridin-2(1H)-one (8.315 g, 49.4 mmol) and Pd/C 10% (1 g) in MeOH (100 mL) and THF (100 mL) was stirred under an atmospheric pressure of H2 at RT for 1.5 hr, filtered through celite, and concentrated. The residue was triturated in Et2O to afford the title compound (6.12 g, 90% yield) as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.94 (s, 3 H) 3.31 (s, 3 H covered by water signal) 4.15 (br s, 2 H) 6.70 (s, 1 H) 6.95 (s, 1 H).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe residue was triturated in Et2O

Sources & evidence

ORD record
ord-0fc3e3d29e674831abd99f223bd68b75
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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