Acetic Acid → N-[2-(2-pyridyl)ethyl]-2-methyl-4-hydroxyaniline

HRID 543916Notes

Reaction equation

HRID 543916 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](O)(=O)[CH3:11].C([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=C>CO>[N:19]1[CH:20]=[CH:21][CH:16]=[CH:17][C:18]=1[CH2:10][CH2:11][NH:4][C:3]1[CH:5]=[CH:6][C:7]([OH:9])=[CH:8][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75024-VinylpyridineHCID 178194-Amino-m-cresol

Product 1

HCID 15597532N-[2-(2-pyridyl)ethyl]-2-methyl-4-hydroxyanilineYield 338.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 50.0 g (0.4 mole) of 2-methyl-4-hydroxyaniline, 2.4 g of glacial acetic acid and 125.0 ml of anhydrous methyl alcohol was heated to reflux with stirring and 63.1 g (0.6 mole) of 4-vinylpyridine was added dropwise. The resulting reaction mixture was refluxed approximately seventy-two hours. After cooling the reaction mixture to ambient temperature, the solid was collected by filtration, washed twice with fresh methanol, and dried in vacuo to obtain 30.9 g of N-2-[2-(4-pyridyl)ethyl]-2-methyl-4-hydroxyaniline (Formula VI: R1 =R9 =H; R2 =CH3 ; R11 =OH), a colored solid which melted at 146°-148.5° C. A significant infrared maximum appeared at 3410 cm-1 (OH;m). The nuclear magnetic resonance spectrum was in accord with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThe resulting reaction mixture
  4. temperaturewas refluxed approximately seventy-two hours
  5. filtrationthe solid was collected by filtration
  6. washwashed twice with fresh methanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ad5e148090a844c394bfd5bdc8b2858d
Source dataset
uspto-grants-1984_05
Patent number
US04447616

Reaction notes

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