Imidazole → 6-(1H-Imidazol-2-yl)-3-nitro-2-pyridinamine

HRID 1974476Notes

Reaction equation

HRID 1974476 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.O>CN(C)C=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([C:13]2[NH:12][CH:16]=[CH:15][N:14]=2)[N:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 27240356-Chloro-3-nitropyridin-2-ylamine

Product 1

HCID 191015706-(1H-Imidazol-2-yl)-3-nitro-2-pyridinamineYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In 80 ml of N,N-dimethylformamide were dissolved 4.00 g of 2-amino-6-chloro-3-nitropyridine and 15.69 g of imidazole, and the solution was stirred at 120° C. overnight. After spontaneous cooling to room temperature, 100 ml of water was added and the resulting crystals were collected by filtration. The crystals were rinsed with a small amount of water and dried under reduced pressure to provide 3.76 g of 2-amino-6-imidazolyl-3-nitropyridine. Physicochemical properties:

Workup

  1. temperatureAfter spontaneous cooling to room temperature
  2. filtrationthe resulting crystals were collected by filtration
  3. washThe crystals were rinsed with a small amount of water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8083c1e4eb534a719866e28c0fed96f7
Source dataset
uspto-grants-1994_02
Patent number
US05283244

Reaction notes

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