3-Methoxyaniline → 4-Carbamoyl-1-(3-methoxyphenyl)pyridinium chloride

HRID 964005Notes

Reaction equation

HRID 964005 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=C(C=CC=1)N>CO>[Cl-:1].[C:2]([C:5]1[CH:10]=[CH:9][N+:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:24][CH3:23])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])[NH2:3]

Participants

4

Reactant 2

HCID 108243-MethoxyanilineHCID 106160034-Carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

Product 1

HCID 106116954-Carbamoyl-1-(3-methoxyphenyl)pyridinium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-carbamoyl-1-(2,4-dinitrophenyl)-pyridinium chloride (43.2 g, prepared in a similar manner to that described in Example 2), 3-methoxyaniline (34 g) and methanol (1500 ml) was stirred at ambient temperature for 16 hours. The mixture was then warmed at 40° C. for 30 minutes, and stirring was continued for 2 hours at ambient temperature, then the solvent was removed in vacuo. Ether was added to the resulting oily solid and the solid collected by filtration. The solid was triturated in hot 2-propanol (11), collected by filtration and dried. The solid was triturated in hot acetone, collected by filtration and dried to give 4-carbamoyl-1-(3-methoxyphenyl)pyridinium chloride as a beige solid (32.4 g), m.p. 272° C. (dec).

Workup

  1. customprepared in a similar manner to that
  2. temperatureThe mixture was then warmed at 40° C. for 30 minutes
  3. stirringstirring
  4. waitwas continued for 2 hours at ambient temperature
  5. customthe solvent was removed in vacuo
  6. additionEther was added to the resulting oily solid
  7. filtrationthe solid collected by filtration
  8. customThe solid was triturated in hot 2-propanol (11)
  9. filtrationcollected by filtration
  10. customdried
  11. customThe solid was triturated in hot acetone
  12. filtrationcollected by filtration
  13. customdried

Sources & evidence

ORD record
ord-313f107eeaaa401f9018feb983532eb0
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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