4,5-Dichloro-6-nitro-2,3-dihydropyridazin-3-one → 4-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

HRID 1111130Notes

Reaction equation

HRID 1111130 reaction equation
[Cl:1][C:2]1[C:3](=[O:12])[NH:4][N:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1Cl.[CH2:13]([O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:20][NH2:21])[CH2:14][CH3:15]>C(O)C>[Cl:1][C:2]1[C:3](=[O:12])[NH:4][N:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH:21][CH2:20][C:19]1[CH:22]=[CH:23][C:24]([O:25][CH3:26])=[C:17]([O:16][CH2:13][CH2:14][CH3:15])[CH:18]=1

Participants

4

Reactant 2

HCID 27823294,5-Dichloro-6-nitro-2,3-dihydropyridazin-3-oneHCID 150790273-n-Propoxy-4-methoxybenzylamine

Product 1

HCID 150790474-chloro-5-(3-n-propoxy-4-methoxybenzylamino)-6-nitro-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 8.0 g of 4,5-dichloro-6-nitro-3(2H)pyridazinone, 29.75 g of 3-n-propoxy-4-methoxybenzylamine and 160 ml of ethanol, was refluxed under stirring for 15 hours. Ethanol was distilled off under reduced pressure, and water was added to the residue thereby obtained. The mixture was extracted with chloroform. The extract was washed with water and dried over sodium sulfate. Then, the solvent was distilled off to obtain an orange solid substance. This product was crystallized from a solvent mixture of methanol-water, to obtain 6.50 g of the above identified compound having a melting point of from 169° to 171° C. as orange crystals.

Workup

  1. temperaturewas refluxed
  2. distillationEthanol was distilled off under reduced pressure, and water
  3. additionwas added to the residue
  4. customthereby obtained
  5. extractionThe mixture was extracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customto obtain an orange solid substance
  10. customThis product was crystallized from a solvent mixture of methanol-water
  11. customto obtain 6.50 g of the
  12. customof from 169° to 171° C.

Sources & evidence

ORD record
ord-bf1a7d5e974b47629128b681ef24a5e3
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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