4-Methoxynaphthalen-1-ylmethylamine → 4-Chloro-5-(4-methoxy-1-naphthylmethylamino)-3(2H)pyridazinone

HRID 1085791

Reaction equation

HRID 1085791 reaction equation
[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1Cl.[CH3:10][O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][NH2:23])=[CH:14][CH:13]=1>C(O)C>[Cl:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[CH:6][C:7]=1[NH:23][CH2:22][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([O:11][CH3:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 591394-Methoxynaphthalen-1-ylmethylamineHCID 732474,5-Dichloro-3-hydroxypyridazine

Product 1

HCID 150071864-Chloro-5-(4-methoxy-1-naphthylmethylamino)-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 330 mg of 4,5-dichloro-3(2H)pyridazinone, 1.12 g of 4-methoxy-1-naphthylmethylamine and 30 ml of ethanol, was refluxed under stirring overnight. The solvent was evaporated under reduced pressure, and a mixture of ethyl acetate and ethyl ether was poured to the residue, whereupon precipitated crystals were collected by filtration. The product was recrystallized from a mixture of methanol/water to obtain 410 mg of the above identified command as slightly yellow crystals having a melting point of from 265° to 266° C.

Workup

  1. temperaturewas refluxed
  2. customThe solvent was evaporated under reduced pressure
  3. additiona mixture of ethyl acetate and ethyl ether
  4. additionwas poured to the residue
  5. customwhereupon precipitated crystals
  6. filtrationwere collected by filtration
  7. customThe product was recrystallized from a mixture of methanol/water
  8. customto obtain 410 mg of the
  9. customof from 265° to 266° C.

Sources & evidence

ORD record
ord-0f9cad209219493591eddaa88cca1417
Source dataset
uspto-grants-1991_04
Patent number
US05011839

Linked notes

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