HCID 67213401, compound → HCID 67212990, compound

HRID 2108387Notes

Reaction equation

HRID 2108387 reaction equation
[N+:1]([CH:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)[CH:7]=[CH:6][NH:5]1)([O-])=O>CO.N.CO>[NH2:1][CH:4]1[N:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:15])[CH:10]=2)[CH:7]=[CH:6][NH:5]1

Participants

4

Reactant 1

HCID 67213401HCID 67213401, compound

Product 1

HCID 67212990HCID 67212990, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21705897Ammonia methanolSolvent

Procedure

A stirred solution of 2-nitro-3-(2-methyl-4-pyridinyl)-1H-imidazole (3.40 g, 16.6 mmol) in 7N methanol/NH3 (70 ml) and methanol (70 ml) was hydrogenated at room temperature on Raney Nickel (2.9 g) for 2 h. The catalyst was removed by filtration and the solution evaporated. The crude product was purified by column chromatography on silica gel (dichloromethane/methanol/NH4OH 40:10:1) to yield 2-amino-3-(2-methyl-4-pyridinyl)-1H-imidazole (1.71 g, 59%) as a green solid. MS (ISP) 175.1 [(M+H)+]; mp 167° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solution evaporated
  3. customThe crude product was purified by column chromatography on silica gel (dichloromethane/methanol/NH4OH 40:10:1)

Sources & evidence

ORD record
ord-077fda0e2f3346acb7298673c3c86c92
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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