Nicotinic Acid → 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine

HRID 257521Notes

Reaction equation

HRID 257521 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](O)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.[NH4+].[OH-]>O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]2[NH:8][C:7]3[C:2]([N:1]=2)=[N:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=1

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 99562,3-DiaminopyridineHCID 14923Ammonium Hydroxide

Product 1

HCID 124055262-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridineYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2,3-diaminopyridine (1.1 g, 10 mmol) and nicotinic acid (1.23 g, 10 mmol) in polyphosphoric acid (15 mL) was heated at 160° C. for 4 hours and poured into 150 mLs of water. The pH was adjusted to pH 8 with NH4OH with cooling. The precipitate was filtered and air dried. Recrystallization from EtOH to give 1.3 g of product (66%), m.p.=133°-135° C. Anal. Calcd. for: C, 67.34; H, 4.11, N, 28.36. Found: C, 67.21; H, 4.04; N, 28.11.

Workup

  1. temperaturewith cooling
  2. filtrationThe precipitate was filtered
  3. customair dried
  4. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-f5132d5bad4745b0ae03c9c95729f068
Source dataset
uspto-grants-1993_11
Patent number
US05262426

Reaction notes

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