4-Aminophenacylpyridinium chloride hydrochloride → 4-Aminophenacylpyridinium chloride

HRID 1281629Notes

Reaction equation

HRID 1281629 reaction equation
[ClH:1].[Cl-].[NH2:3][C:4]1[CH:18]=[CH:17][C:7]([C:8](=[O:16])[CH2:9][N+:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>O>[Cl-:1].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8](=[O:16])[CH2:9][N+:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 1

HCID 227152914-Aminophenacylpyridinium chloride hydrochloride

Product 1

HCID 227152884-Aminophenacylpyridinium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Two grams of the obtained 4-aminophenacylpyridinium chloride hydrochloride was dissolved in 15 g of water, and 4.5 g of a basic ion exchange resin (Amberlite IRA400-OH) was added thereto. The mixture was stirred, and filtered to remove the ion exchange resin. Thereby an aqueous solution of 4-aminophenacylpyridinium chloride was obtained. The aqueous solution of 1.3 g of 4-aminophenacylpyridinium chloride in 25 g of water was refluxed with 1 g of silver nitrate for 90 minutes. The formed precipitate was removed by filtration. To the filtrate, was added 5 g of carbon black having a specific surface area of 200 m2/g, and DBPA of 122 mL/100 g. The mixture was heated to about 80° C. Thereto, were added 0.52 g of concentrated hydrochloric acid, and a solution of sodium nitrite in a small amount of water, successively. The dispersion was stirred further for 1.5 hours. Thereby, a diazonium salt having a NN+C6H4COCH2(N+C5H5) group of the structure shown below was formed. This formed salt reacted with the carbon black.

Workup

  1. filtrationfiltered
  2. customto remove the ion exchange resin

Sources & evidence

ORD record
ord-72343e2d023f4146b4e304b4c0236f4a
Source dataset
uspto-grants-2002_09
Patent number
US06454403B1

Reaction notes

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