Isonicotinic Acid → HCID 12405523, compound

HRID 1156508Notes

Reaction equation

HRID 1156508 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[C:13]([NH2:18])[CH:12]=1.[NH4+].[OH-]>>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]2[N:17]=[C:1]([C:2]3[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=3)[NH:18][C:13]=2[CH:12]=1

Participants

4

Reactant 3

HCID 5922Isonicotinic AcidHCID 72634-Chloro-1,2-diaminobenzeneHCID 14923Ammonium Hydroxide

Product 1

HCID 12405523HCID 12405523, compoundYield 49.1%

Procedure

To a mixture of isonicotinic acid (4.9 g., 0.04 mol) and 4-chloro-o-phenylenediamine (5.8 g., 0.041 mol) was added polylphosphoric acid (20 ml.). The mixture was heated to 200° and maintained at this temperature for 45 min. After cooling, the reaction mixture was poured onto ice and the solution made basic with conc. NH4OH. The resulting yellow solid was removed by filtration, dissolved in isopropanol, filtered and the filtrate concentrated to a solid. After recrystallization from EtOH-H2O, 4.5 g. of 5-chloro-2-(4-pyridyl)benzimidazole (49.1%) was obtained; m.p. 306-307.

Workup

  1. additionwas added polylphosphoric acid (20 ml.)
  2. temperatureThe mixture was heated to 200°
  3. temperaturemaintained at this temperature for 45 min
  4. temperatureAfter cooling
  5. additionthe reaction mixture was poured onto ice
  6. customThe resulting yellow solid was removed by filtration
  7. dissolutiondissolved in isopropanol
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated to a solid
  10. customAfter recrystallization from EtOH-H2O, 4.5 g

Sources & evidence

ORD record
ord-20b16434815e4592a8fb49a83b89e3b2
Source dataset
uspto-grants-1982_06
Patent number
US04336257

Reaction notes

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