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

HRID 2204303Notes

Reaction equation

HRID 2204303 reaction equation
[Cl:1][C:2]1[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>CO.[Ni]>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=1

Participants

4

Reactant 1

HCID 867031063-chloro-1-methyl-5-nitropyridin-2(1H)-one

Product 1

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Ra—Ni (EtOH) (230 mmol) was added to a solution of 3-chloro-1-methyl-5-nitro-1H-pyridin-2-one (Step E6) (136 mmol) in MeOH (400 mL) and the mixture was stirred at rt under a hydrogen atmosphere for 97 h. The reaction mixture was filtered over celite and concentrated. The product was purified by flash chromatography to afford the title compound as a black solid. ESI-MS: tR=0.33 min, [M+H]+ 159/161 (LC-MS 1); TLC: Rf=0.28 (9:1 CH2Cl2/MeOH).

Workup

  1. filtrationThe reaction mixture was filtered over celite and
  2. concentrationconcentrated
  3. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-3866cf8cd26a425ab2cc2199095c3874
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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