1,5-Dimethyl-3-nitropyridin-2-one → 3-Amino-1,5-dimethyl-1,2-dihydropyridin-2-one

HRID 869083Notes

Reaction equation

HRID 869083 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]1=[O:12]>CO.[Ni]>[NH2:9][C:4]1[C:3](=[O:12])[N:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

4

Reactant 1

HCID 51067591,5-Dimethyl-3-nitropyridin-2-one

Product 1

HCID 717562163-Amino-1,5-dimethyl-1,2-dihydropyridin-2-oneYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 9.74 g (57.9 mmol) 1,5-dimethyl-3-nitropyridin-2(1H)-one (product from step 199.5), 2 g (57.9 mmol) Raney-Ni in 230 ml methanol was shaken in a duck glass under H2 atmosphere for 16 hours. After that, the mixture was filtered over celite, washed with MeOH, concentrated in vacuum and dried at high vacuum over night to obtain 7.9 g (57.2 mmol, 99% yield) of the title compound as a brownish solid. LCMS: (M+H)=139; tR=0.43 min (LC-MS 6). HPLC: tR=1.22 min (HPLC 8). 1H-NMR (DMSO-d6, 400 MHz) δ ppm 6.67 (m, 1H) 6.30 (m, 1H) 5.05 (bs, 2H) 3.38 (s, 3H) 1.93 (s, 3H).

Workup

  1. filtrationAfter that, the mixture was filtered over celite
  2. washwashed with MeOH
  3. concentrationconcentrated in vacuum
  4. customdried at high vacuum over night

Sources & evidence

ORD record
ord-7e550b70526e45ccb5acbf160a7af81e
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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