Water → HCID 13987686, compound

HRID 2231680Notes

Reaction equation

HRID 2231680 reaction equation
[Cl:1][C:2]1[C:3](=[O:11])[N:4]([CH2:9][CH3:10])[N:5]=[CH:6][C:7]=1Cl.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[Cl:1][C:2]1[C:3](=[O:11])[N:4]([CH2:9][CH3:10])[N:5]=[CH:6][C:7]=1[NH:22][CH2:21][CH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4657O-MethyltyramineHCID 11430Potassium CarbonateHCID 6764264,5-dichloro-2-ethyl-3(2H)-pyridazinone

Product 1

HCID 13987686HCID 13987686, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture comprising 0.5 g of 4,5-dichloro-2-ethyl-3(2H)pyridazinone, 1.18 g of 4-methoxyphenylethylamine, 0.36 g of potassium carbonate, 18 ml of water and 6 ml of 1,4-dioxane, was refluxed under stirring for 8 hours. Then, 1,4-dioxane was distilled off under reduced pressure, and the residue thereby obtained was extracted with ethyl acetate. The extract was washed sequentially with dilute hydrochloric acid and water, and dried over sodium sulfate. Then, 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, whereby 400 mg of the above identified compound was obtained as colorless crystals having a melting point of from 135° to 135.5° C.

Workup

  1. temperaturewas refluxed
  2. distillationThen, 1,4-dioxane was distilled off under reduced pressure
  3. customthe residue thereby obtained
  4. extractionwas extracted with ethyl acetate
  5. washThe extract was washed sequentially with dilute hydrochloric acid and water
  6. dry with materialdried over sodium sulfate
  7. distillationThen, solvent was distilled off
  8. customThe residue was purified by silica gel column chromatography
  9. customwas obtained as colorless crystals
  10. customof from 135° to 135.5° C.

Sources & evidence

ORD record
ord-11494ada93ed45a8b5f527ba27095d84
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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