Potassium Carbonate → 4-chloro-5-(3-benzyloxybenzylamino)-2-i-propyl-3(2H)pyridazinone

HRID 2372345Notes

Reaction equation

HRID 2372345 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][NH2:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:18]([N:21]1[C:26](=[O:27])[C:25]([Cl:28])=[C:24](Cl)[CH:23]=[N:22]1)([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O>[Cl:28][C:25]1[C:26](=[O:27])[N:21]([CH:18]([CH3:19])[CH3:20])[N:22]=[CH:23][C:24]=1[NH:14][CH2:13][C:12]1[CH:15]=[CH:16][CH:17]=[C:10]([O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 123518304,5-Dichloro-2-isopropylpyridazin-3(2H)-oneHCID 19744718[3-(Benzyloxy)phenyl]methanamine hydrochloride

Product 1

HCID 138538954-chloro-5-(3-benzyloxybenzylamino)-2-i-propyl-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 8.24 g of 3-benzyloxybenzylamine hydrochloride prepared in Reference Example 2A, 3.11 g of 2-i-propyl-4,5-dichloro-3(2H)pyridazinone, 7.26 g of potassium carbonate, 30 ml of 1,4-dioxane and 90 ml of water was refluxed under stirring for 4.5 hours. The majority of 1,4-dioxane was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with diluted hydrochloric acid, and then treated with cerite to remove the precipitate. The organic layer was separated, and washed with water and a saturated sodium chloride aqueous solution, and then dried over sodium sulfate. Then, the solvent was distilled off. The pale yellow oily substance thereby obtained was crystallized from ether-n-hexane to obtain 2.51 g of the above identified compound having a melting point of from 106° to 108° C. as colorless crystals.

Workup

  1. temperaturewas refluxed
  2. distillationThe majority of 1,4-dioxane was distilled off under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with diluted hydrochloric acid
  5. additiontreated with cerite
  6. customto remove the precipitate
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materiala saturated sodium chloride aqueous solution, and then dried over sodium sulfate
  10. distillationThen, the solvent was distilled off
  11. customThe pale yellow oily substance thereby obtained
  12. customwas crystallized from ether-n-hexane
  13. customto obtain 2.51 g of the
  14. customof from 106° to 108° C.

Sources & evidence

ORD record
ord-3ae325809fc1455a8f52bb207ff2edc4
Source dataset
uspto-grants-1992_03
Patent number
US05098900

Reaction notes

Loading…