N-(6-Chloro-3-nitro-2-pyridyl)-alanine methyl ester → (3S)-6-Chloro-3-methyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-one

HRID 21529Notes

Reaction equation

HRID 21529 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH3:16])[NH:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[C:8]([Cl:15])[N:7]=1>CO.[Ni].[H][H]>[Cl:15][C:8]1[N:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[NH:12][C:3](=[O:2])[C@H:4]([CH3:16])[NH:5]2

Participants

5

Reactant 1

HCID 54223679N-(6-Chloro-3-nitro-2-pyridyl)-alanine methyl ester

Product 1

HCID 57066600(3S)-6-Chloro-3-methyl-3,4-dihydro-1,4,5-triazanaphthalen-2(1H)-oneYield 24.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

Compound A (9.0 g, 0.05 mol) was dissolved in 200 ml of methanol and hydrogenated with Raney nickel catalysis under 1 atm of hydrogen. After hydrogen uptake ceased, the catalyst was filtered off with suction, and the solvent was removed in vacuo. The solid product was stirred with diethyl ether, resulting in 2.4 g of pure product (melting point 236°-237° C.).

Workup

  1. filtrationthe catalyst was filtered off with suction
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5258b6096853476d98abfadcef3fd9e0
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Reaction notes

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