Hydrazine hydrate (1:1) → 6-[4-(3-aminopropyl)-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 1590791Notes

Reaction equation

HRID 1590791 reaction equation
C1(=O)N(CCCO[C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)=[CH:12][C:11]=2[Cl:23])C(=O)C2=CC=CC=C12.O.NN>C(O)(C)C>[NH2:20][CH2:19][CH2:18][CH2:17][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:12][C:11]=1[Cl:23]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 150163646-[4-(3-phthalimidopropyloxy)-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 197682576-[4-(3-aminopropyl)-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 122.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5.4 g (13.1 mmol) of the phthalimide prepared above and 700 microliters (14.4 mmol) of hydrazine monohydrate in 150 ml of isopropanol is heated at reflux overnight. The solvent is removed under vacuum, the residue is taken up in 15 ml of 70:30 (CH3OH:NH4OH) and flash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH) to give 2.13 g of 6-[4-(3-aminopropyl)-3-chlorophenyl]-4,5-dihydro-3(2H)-pyridazinone as a pale yellow solid. Yield, 58%.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. customThe solvent is removed under vacuum
  4. customchromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH)

Sources & evidence

ORD record
ord-2612e48ca45646418acce6f8edf4dac8
Source dataset
uspto-grants-1993_04
Patent number
US05204463

Reaction notes

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