Aniline → 4-Carbamoyl-1-phenylpyridinium chloride

HRID 963997Notes

Reaction equation

HRID 963997 reaction equation
[Cl-:1].[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][C:14]([N+]([O-])=O)=[CH:13][C:12]=2[N+]([O-])=O)=[CH:7][CH:6]=1)(=[O:4])[NH2:3].NC1C=CC=CC=1>CO>[Cl-:1].[C:2]([C:5]1[CH:6]=[CH:7][N+:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)(=[O:4])[NH2:3]

Participants

4

Reactant 2

HCID 6115AnilineHCID 106160034-Carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

Product 1

HCID 107048844-Carbamoyl-1-phenylpyridinium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride (50 g, prepared in a similar manner to that described in Example 2), aniline (35 ml) and methanol (11) was stirred at ambient temperature for 48 hours. The resulting suspension was heated at 50° C. for 1 hour, then cooled and the solvent removed in vacuo. The solid residue was triturated with acetone (2×11) then collected by filtration to give 4-carbamoyl-1-phenylpyridinium chloride (33.24 g), mp 290°-292° C.

Workup

  1. customprepared in a similar manner to that
  2. temperatureThe resulting suspension was heated at 50° C. for 1 hour
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. customThe solid residue was triturated with acetone (2×11)
  6. filtrationthen collected by filtration

Sources & evidence

ORD record
ord-f647a45feb8b41c5ad0f416ef5c76f45
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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