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

HRID 2308955Notes

Reaction equation

HRID 2308955 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 of 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-9fa91f7458bc4c77924072cfba3d58ff
Source dataset
uspto-grants-1987_09
Patent number
US04692443

Reaction notes

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