Phthalimide → 6-[4-(3-aminopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 344639Notes

Reaction equation

HRID 344639 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]([CH3:23])[CH2:18][C:19](=[O:22])[NH:20][N:21]=3)=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.O.NN.C1(=O)NC(=O)C2=CC=CC=C12.NN>CO.C(Cl)(Cl)Cl.C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]([CH3:23])[CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 6809PhthalimideHCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 150163386-[4-(3-phthalimidopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 144032876-[4-(3-aminopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneYield 80%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 0.997 g (2.55 mmol) of the phthalimide prepared above, 124 microliters (2.55 mmol) of 98% hydrazine monohydrate, and 25 ml of ethanol is heated at reflux under N2 overnight. TLC (90:10 CHCl3 :CH3OH) of the reaction mixture showed some phthalimide still present. An additional 25 ml of hydrazine was added, and the mixture heated at reflux for 3 hrs. The solvent is removed under vacuum, the residue taken up in about 10 ml of CH3OH and flash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH) to give 531 mg of 6-[4-(3-aminopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)pyridazinone as a white solid. Yield 80%.

Workup

  1. temperatureis heated
  2. temperatureat reflux under N2 overnight
  3. temperaturethe mixture heated
  4. temperatureat reflux for 3 hrs
  5. customThe solvent is removed under vacuum
  6. customflash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH)

Sources & evidence

ORD record
ord-9e74117846294d748f13f9c30b221952
Source dataset
uspto-grants-1991_10
Patent number
US05053338

Reaction notes

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