2-Methoxyaniline → 4-Carbamoyl-1-(2-methoxyphenyl)-pyridinium chloride

HRID 963986Notes

Reaction equation

HRID 963986 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].[CH3:23][O:24]C1C=CC=CC=1N>CO>[Cl-:1].[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:24][CH3:23])=[CH:7][CH:6]=1)(=[O:4])[NH2:3]

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 106160034-Carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

Product 1

HCID 106353734-Carbamoyl-1-(2-methoxyphenyl)-pyridinium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-carbamoyl-1-(2,4-dinitrophenyl)-pyridinium chloride (13.6 g), 2-methoxyaniline (10 ml) and methanol (500 ml) was stirred at ambient temperature for 16 hours and the solvent was removed in vacuo. Ether containing a small amount of acetone was added and the mixture heated under reflux until solidification of the product was complete. The product was collected by filtration to give 4-carbamoyl-1-(2-methoxyphenyl)-pyridinium chloride as a yellow solid (11.5 g), m.p. 229°-230° C. (dec).

Workup

  1. customthe solvent was removed in vacuo
  2. additionEther containing a small amount of acetone was added
  3. temperaturethe mixture heated
  4. temperatureunder reflux until solidification of the product
  5. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-c04ca881ae73424bab6d8c70154e9363
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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