Isonicotinic Acid → HCID 12405523, compound

HRID 1278175Notes

Reaction equation

HRID 1278175 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 polyphosphoric 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. temperatureThe mixture was heated to 200°
  2. temperaturemaintained at this temperature for 45 min
  3. temperatureAfter cooling
  4. additionthe reaction mixture was poured onto ice
  5. customThe resulting yellow solid was removed by filtration
  6. dissolutiondissolved in isopropanol
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated to a solid
  9. customAfter recrystallization from EtOH-H2O, 4.5 g

Sources & evidence

ORD record
ord-eafdee6eef754ca4b9d01d4a8508eb69
Source dataset
uspto-grants-1981_07
Patent number
US04281005

Reaction notes

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