3,4-Diaminopyridine → 1H-Imidazo(4,5-c)pyridine

HRID 1253217Notes

Reaction equation

HRID 1253217 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[C:9](OC(OCC)OCC)(=O)C>C(OCC)(=O)C>[N:8]1[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[NH:1][CH:9]=1

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 84166Methanol, 1,1-diethoxy-, 1-acetate

Product 1

HCID 92271H-Imidazo(4,5-c)pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3H-Imidazolo[4,5-c]pyridine was prepared by the method of Stanovik and Tisler, Synthesis, 2, 120 (1974). A mixture of 2.2 g (0.02 mole) of 3,4-diaminopyridine and 5 ml diethoxymethyl acetate was heated at reflux for two hours. The reaction mixture was cooled and diluted by addition of ethyl acetate. The solid precipitate was collected by filtration and sublimed at 170° C. and 50 torr to give 0.84 g of 3H-imidazolo[4,5-c]pyridine; mp 165°-168° C.

Workup

  1. custom3H-Imidazolo[4,5-c]pyridine was prepared by the method of Stanovik and Tisler, Synthesis, 2, 120 (1974)
  2. temperaturewas heated
  3. temperatureat reflux for two hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationThe solid precipitate was collected by filtration
  6. customsublimed at 170° C.

Sources & evidence

ORD record
ord-74de035ae5704b3d99299a5f2d9df498
Source dataset
uspto-grants-1988_05
Patent number
US04748172

Reaction notes

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