2-(Ethoxymethylene)propanedinitrile → 3,7-dip-tolyl-3H-imidazo[4,5-b]pyridine

HRID 19447

Reaction equation

HRID 19447 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:13]([NH2:14])=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:3][CH:2]=1.[CH2:23](OC=C(C#N)C#N)C>C(O)(C)C>[C:1]1([CH3:22])[CH:2]=[CH:3][C:4]([N:7]2[C:8]3=[N:9][CH:10]=[CH:11][C:12]([C:15]4[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=4)=[C:13]3[N:14]=[CH:23]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 86622263N2,4-dip-tolylpyridine-2,3-diamine

Product 1

HCID 685578823,7-dip-tolyl-3H-imidazo[4,5-b]pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.70 mol of N2,4-dip-tolylpyridine-2,3-diamine and 2.56 mol of 2-(ethoxymethylene)malonnitrile were added in 10 ml of isopropanol, and refluxed for 6 hours. The solution was removed and was purified by using column chromatography to thereby produce a solid crystalline product at a yield of 84%.

Workup

  1. temperaturerefluxed for 6 hours
  2. customThe solution was removed
  3. customwas purified
  4. customto thereby produce a solid crystalline product at a yield of 84%

Sources & evidence

ORD record
ord-28dfca87989749a49ff2d38ea0776f26
Source dataset
uspto-grants-2010_06
Patent number
US07745020B2

Linked notes

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