Potassium Carbonate → 4-Chloro-5-[3-(2-n-propyl-4-cyanophenoxy)-2-hydroxypropoxy]-2-i-propyl-3(2H)pyridazinone

HRID 2231683Notes

Reaction equation

HRID 2231683 reaction equation
[Cl:1][C:2]1[C:3](=[O:16])[N:4]([CH:13]([CH3:15])[CH3:14])[N:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:12][O:11]1.[CH2:17]([C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1[OH:28])[CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>C(C(CC)=O)C>[Cl:1][C:2]1[C:3](=[O:16])[N:4]([CH:13]([CH3:15])[CH3:14])[N:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([OH:11])[CH2:12][O:28][C:21]1[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:20]=1[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 139876694-hydroxy-3-propylBenzonitrileHCID 139878384-chloro-5-(2-oxiranylmethoxy)-2-i-propyl-3(2H)pyridazinone

Product 1

HCID 139877974-Chloro-5-[3-(2-n-propyl-4-cyanophenoxy)-2-hydroxypropoxy]-2-i-propyl-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

A mixture comprising 2.0 g of 4-chloro-5-(2-oxiranylmethoxy)-2-i-propyl-3(2H)pyridazinone prepared in Reference Example 5, 1.5 g of 2-n-propyl-4-cyanophenol, 1.35 g of potassium carbonate and 80 ml of diethyl ketone, was refluxed under stirring for 8 hours. Then, diethyl ketone was distilled off under reduced pressure, and the residue thereby obtained was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate. Then, the solvent was distilled off. The residue was purified by silica gel column chromatography by using benzene-ethyl acetate (1:1, v/v) as the developer. The colorless crystals thereby obtained was recrystallized from ethyl ether to obtain 1.3 g of the above identified compound as colorless crystals having a melting point of from 118.5° to 121° C.

Workup

  1. temperaturewas refluxed
  2. distillationThen, diethyl ketone was distilled off under reduced pressure
  3. customthe residue thereby obtained
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography
  9. customThe colorless crystals thereby obtained
  10. customwas recrystallized from ethyl ether
  11. customto obtain 1.3 g of the
  12. customof from 118.5° to 121° C.

Sources & evidence

ORD record
ord-0c48ec2be8324e34a6f77589fc5c14ce
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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