3,4,5-Trichlor-6-hydroxypyridazin → 4,6-dichloro-5-(3-n-propoxy-4-methoxybenzylamino)-3(2H)pyridazinone

HRID 1111138Notes

Reaction equation

HRID 1111138 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[NH:4][N:5]=[C:6]([Cl:9])[C:7]=1Cl.[CH2:11]([O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:18][NH2:19])[CH2:12][CH3:13]>C(O)C>[Cl:1][C:2]1[C:3](=[O:10])[NH:4][N:5]=[C:6]([Cl:9])[C:7]=1[NH:19][CH2:18][C:17]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:15]([O:14][CH2:11][CH2:12][CH3:13])[CH:16]=1

Participants

4

Reactant 2

HCID 111063493,4,5-Trichlor-6-hydroxypyridazinHCID 150790273-n-Propoxy-4-methoxybenzylamine

Product 1

HCID 150790944,6-dichloro-5-(3-n-propoxy-4-methoxybenzylamino)-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 997 mg of 4,5,6-trichloro-3(2H)pyridazinone, 3.20 g of 3-n-propoxy-4-methoxybenzylamine and 30 ml of ethanol, was refluxed under stirring for 2 hours. Ethanol was distilled off under reduced pressure, and dilute hydrochloric acid was poured into the residue thereby obtained. The mixture was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate. Then, the solvent was distilled off to obtain a light brown viscous oily substance. The residue was subjected to silica gel column chromatography, and the second fraction obtained by eluting with a solvent mixture of benzene-ethyl acetate (2.5:1 v/v) was separated to obtain a colorless solid substance. The product was crystallized from a solvent solution of methanol-diethyl ether, to obtain 513 mg of the above identified compound having a melting point of from 181° to 183° C. as colorless crystals.

Workup

  1. temperaturewas refluxed
  2. distillationEthanol was distilled off under reduced pressure, and dilute hydrochloric acid
  3. additionwas poured into the residue
  4. customthereby obtained
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customto obtain a light brown viscous oily substance
  10. customthe second fraction obtained
  11. washby eluting with a solvent mixture of benzene-ethyl acetate (2.5:1 v/v)
  12. customwas separated
  13. customto obtain a colorless solid substance
  14. customThe product was crystallized from a solvent solution of methanol-diethyl ether
  15. customto obtain 513 mg of the
  16. customof from 181° to 183° C.

Sources & evidence

ORD record
ord-a04a783f454e440fa4800ffbe599967c
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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