Ethylene Glycol → 2-[(4-Amino-3,5-dichloropyridin-2-yl)oxy]ethan-1-ol

HRID 1833288Notes

Reaction equation

HRID 1833288 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4](Cl)[C:3]=1[Cl:10].[OH-].[K+].[CH2:13]([OH:16])[CH2:14][OH:15]>>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([O:15][CH2:14][CH2:13][OH:16])[C:3]=1[Cl:10]

Participants

4

Reactant 3

HCID 174Ethylene Glycol2×HCID 14797Potassium HydroxideHCID 7286762,3,5-trichloropyridin-4-amine

Product 1

HCID 213886662-[(4-Amino-3,5-dichloropyridin-2-yl)oxy]ethan-1-ol

Conditions

Temperature
108 °C

Procedure

A mixture of 200 grams (1.1 mole) of 4-amino-2,3,5-trichloropyridine in 500 milliliters of ethylene glycol was heated at 108° C., with agitation, until a solution was obtained. To this solution was added over a 20-minute period, while the temperature was raised to 123° C., a solution of 70 grams (1.25 mole) of potassium hydroxide dissolved in 300 milliliters of ethylene glycol. The temperature was raised to 150°-151° C. and agitation was maintained for 2 hours. The reaction mixture was cooled and filtered under reduced pressure. The filtrate was diluted with 1500 milliliters of cold water and extracted with methylene chloride. The solvent was removed by evaporation under reduced pressure. The liquid residue which remained was crystallized from hexane and dissolved in hot chloroform. The solution was cooled and the 4-amino-3,5-dichloro-2-(2-hydroxyethoxy)pyridine product was recovered by filtration under reduced pressure. The purified product was recovered in a yield of 75 grams which melted at 77.5°- 81° C.

Workup

  1. customwas obtained
  2. additionTo this solution was added over a 20-minute period, while the temperature
  3. temperaturewas raised to 123° C.
  4. temperatureThe temperature was raised to 150°-151° C.
  5. temperatureagitation was maintained for 2 hours
  6. temperatureThe reaction mixture was cooled
  7. filtrationfiltered under reduced pressure
  8. additionThe filtrate was diluted with 1500 milliliters of cold water
  9. extractionextracted with methylene chloride
  10. customThe solvent was removed by evaporation under reduced pressure
  11. customThe liquid residue which remained was crystallized from hexane
  12. dissolutiondissolved in hot chloroform
  13. temperatureThe solution was cooled
  14. filtrationthe 4-amino-3,5-dichloro-2-(2-hydroxyethoxy)pyridine product was recovered by filtration under reduced pressure
  15. customThe purified product was recovered in a yield of 75 grams which melted at 77.5°- 81° C.

Sources & evidence

ORD record
ord-72ea24f517b14e8892e0b4507757f3ab
Source dataset
uspto-grants-1978_01
Patent number
US04066438

Reaction notes

Loading…