3,4-Diaminopyridine → HCID 178505655, compound

HRID 1200227Notes

Reaction equation

HRID 1200227 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[F:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=O.[OH-].[Na+]>O>[F:9][C:10]1[CH:11]=[C:12]([C:13]2[NH:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[N:1]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 59183,4-DiaminopyridineHCID 99683-Fluorobenzoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 178505655HCID 178505655, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3,4-diaminopyridine (1.09 g., 10 mmoles), 3-fluorobenzoic acid (1.40 g., 10 mmoles), and polyphosphoric acid (PPA, 40 g.) was heated to about 200° C. with stirring for 3.5 hours. The solution was then slowly added to water. The solution was then neutralized by the addition of 50% aqueous sodium hydroxide and the resulting precipitate was collected by filtration. Crystallization from isopropanol/water gave 1.72 g. (81% yield) of 2-(3-fluorophenyl)imidazo[4,5-c]pyridine (base), m.p. about 290°-291° C.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customCrystallization from isopropanol/water
  3. customgave 1.72 g

Sources & evidence

ORD record
ord-f7887659e7a44cbca2184917c2f31e3e
Source dataset
uspto-grants-1990_02
Patent number
US04904785

Reaction notes

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