Methanol → HCID 15597531, compound

HRID 543919Notes

Reaction equation

HRID 543919 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[CH2:10].CO.[OH-].[Na+]>O.C(O)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:9][CH2:10][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([OH:1])[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 75212-VinylpyridineHCID 115683-AminophenolHCID 14798Sodium Hydroxide

Product 1

HCID 15597531HCID 15597531, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

With stirring a mixture of 44.0 g of 3-hydroxyaniline, 60.0 g of 2-vinylpyridine, 140.0 ml of methyl alcohol and 5.0 ml of glacial acetic acid was maintained at reflux temperature for approximately twenty-four hours. The methyl alcohol was removed by distillation and a mixture of water and toluene was added to the resultant residue. Three layers resulted. Sufficient 5 percent aqueous sodium hydroxide was added to adjust the water layer to approximately pH 7. The bottom oil layer was separated, and dried under reduced pressure to obtain a gummy solid which was triturated with hexane to obtain 69.0 g of N-[2-(2-pyridyl)ethyl]-3-hydroxyaniline(Formula V: R4 =R9 =H; R10 =OH), a pale tan solid which after being exposed to air turned into a taffy-like solid. The nuclear magnetic resonance spectrum was concordant with the assigned structure. The water layer was discarded. The toluene layer was washed first with water and then with saturated sodium chloride solution and evaporated to dryness under reduced pressure. The residue was recrystallized from a mixture of ispropanol and hexane to obtain 3.9 g of N-[2-(2-pyridyl)ethyl]-3-hydroxyaniline, a white solid which melted at 118°-120° C. A significant infrared maximum appeared at 1195 cm-1 (N--C;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure.

Workup

  1. temperaturewas maintained
  2. temperatureat reflux temperature for approximately twenty-four hours
  3. customThe methyl alcohol was removed by distillation
  4. additiona mixture of water and toluene
  5. additionwas added to the resultant residue
  6. customThree layers resulted
  7. customThe bottom oil layer was separated
  8. customdried under reduced pressure
  9. customto obtain a gummy solid which
  10. customwas triturated with hexane

Sources & evidence

ORD record
ord-40f0b1b1e7da45c3ab5a8994ded265fe
Source dataset
uspto-grants-1984_05
Patent number
US04447616

Reaction notes

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