2-Chloroaniline → 4-Carbamoyl-1-(2-chlorophenyl)-pyridinium chloride

HRID 964007Notes

Reaction equation

HRID 964007 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].[Cl:23]C1C=CC=CC=1N>CO>[Cl-:23].[C:2]([C:5]1[CH:6]=[CH:7][N+:8]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[Cl:1])=[CH:9][CH:10]=1)(=[O:4])[NH2:3]

Participants

4

Reactant 2

HCID 72402-Chloroaniline3×HCID 106160034-Carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

Product 1

HCID 107544174-Carbamoyl-1-(2-chlorophenyl)-pyridinium chlorideYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-carbamoyl-1-(2,4-dinitrophenyl)-pyridinium chloride (41 g) and 2-chloroaniline (20 g) in methanol (500 ml) was stirred at ambient temperature for 24 hours. The mixture was then heated under reflux for 24 hours and then a further portion of 2-chloroaniline (10 g) was added. Heating under reflux was continued for a further 48 hours then another portion of 2-chloroaniline (10 g) was added. The mixture was heated for a further 48 hours, then cooled and the solvent removed in vacuo. The residue was triturated with hot acetone (2×11), cooled and the solid collected by filtration. The solid was dissolved in hot methanol (100 ml), treated with charcoal and hot filtered. Hot ethyl acetate (500 ml) was added to the filtrate and the solution was allowed to cool. The resulting solid was collected by filtration, washed with ethyl acetate and dried to give crude 4-carbamoyl-1-(2-chlorophenyl)-pyridinium chloride (23.69 g) which was used without further purification.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 24 hours
  3. temperatureHeating
  4. temperatureunder reflux
  5. waitwas continued for a further 48 hours
  6. temperatureThe mixture was heated for a further 48 hours
  7. temperaturecooled
  8. customthe solvent removed in vacuo
  9. customThe residue was triturated with hot acetone (2×11)
  10. temperaturecooled
  11. filtrationthe solid collected by filtration
  12. dissolutionThe solid was dissolved in hot methanol (100 ml)
  13. additiontreated with charcoal and hot filtered
  14. additionHot ethyl acetate (500 ml) was added to the filtrate
  15. temperatureto cool
  16. filtrationThe resulting solid was collected by filtration
  17. washwashed with ethyl acetate
  18. customdried

Sources & evidence

ORD record
ord-fbb7a13c90b74479ab10512d9c206298
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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