4,5-Dibromo-2,3-dihydropyridazin-3-one → 4-bromo-5-(3-n-propoxy-4-methoxy-N-methylbenzylamino)-3(2H)pyridazinone

HRID 1111129Notes

Reaction equation

HRID 1111129 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1Br.[CH2:10]([O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH2:17][NH:18][CH3:19])[CH2:11][CH3:12]>C(O)C>[Br:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[N:18]([CH2:17][C:16]1[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:14]([O:13][CH2:10][CH2:11][CH3:12])[CH:15]=1)[CH3:19]

Participants

4

Reactant 2

HCID 2361814,5-Dibromo-2,3-dihydropyridazin-3-oneHCID 150790253-n-propoxy-4-methoxy-N-methylbenzylamine

Product 1

HCID 150790334-bromo-5-(3-n-propoxy-4-methoxy-N-methylbenzylamino)-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 300 mg of 4,5-dibromo-3(2H)pyridazinone, 740 mg of 3-n-propoxy-4-methoxy-N-methylbenzylamine and 10 ml of ethanol, was refluxed under stirring for 7 hours. Then, ethanol was distilled off under reduced pressure, dilute hydrochloric acid was added to the residue thereby obtained, and the mixture was extracted with ethyl acetate. The extract was washed twice with water and dried over sodium sulfate. Then, the solvent was distilled off to obtain a yellow solid substance. The product was crystallized from ethyl acetate, to obtain 310 mg of the above identified compound having a melting point of from 149° to 150° C. as light yellow crystals.

Workup

  1. temperaturewas refluxed
  2. distillationThen, ethanol was distilled off under reduced pressure, dilute hydrochloric acid
  3. additionwas added to the residue
  4. customthereby obtained
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed twice with water
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customto obtain a yellow solid substance
  10. customThe product was crystallized from ethyl acetate
  11. customto obtain 310 mg of the
  12. customof from 149° to 150° C.

Sources & evidence

ORD record
ord-f77e773daec44d45a51f9b111b6c1a40
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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