HCID 19932873, compound → HCID 19932785, compound

HRID 21533Notes

Reaction equation

HRID 21533 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:15])([CH3:14])[C:10](OC)=[O:11])[C:5]([N+:16]([O-])=O)=[CH:4][CH:3]=1.[H][H]>CO.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:16][C:10](=[O:11])[C:9]([CH3:15])([CH3:14])[NH:8]2

Participants

5

Reactant 2

HCID 19932873HCID 19932873, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19932785HCID 19932785, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Methyl N-(6-chloro-3-nitro-2-pyridyl)-2-aminoisobutyrate (4.0 g, 14.6 mmol) was hydrogenated in 250 ml of methanol with Raney nickel catalysis under 1 atm of hydrogen. After hydrogen uptake ceased, the catalyst was filtered off with suction, and the filtrate was concentrated and chromatographed on silica gel (ethyl acetate/heptane=1:2). 1.89 g (61%) of the compound of Example 15, of melting point 229° C., were obtained.

Workup

  1. filtrationthe catalyst was filtered off with suction
  2. concentrationthe filtrate was concentrated
  3. customchromatographed on silica gel (ethyl acetate/heptane=1:2)

Sources & evidence

ORD record
ord-cc4af762ad524c07840cce09b6104c77
Source dataset
uspto-grants-1995_06
Patent number
US05424311

Reaction notes

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