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

HRID 344643Notes

Reaction equation

HRID 344643 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[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)=[CH:12][CH:11]=2)C(=O)C2=CC=CC=C12.O.NN>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[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 144418626-[4-(3-phthalimidopropyloxy)phenyl]-4,5-dihydro3(2H)-pyridazinone

Product 1

HCID 144418676-[4-(3-aminopropoxy)phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 51.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.748 g (7.28 mmol) of the phthalimide prepared above and 398 microliters (8.0 mmol) of 98% hydrazine hydrate in 75 ml of ethanol is heated overnight at reflux under N2. After cooling to RT, the volatiles are removed under vacuum. The residual white solid 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 929 mg of 6-[4-(3-aminopropyloxy)phenyl]-4,5-dihydro-3(2H)-pyridazinone as a white solid. Yield, 23%.

Workup

  1. temperatureis heated overnight
  2. temperatureat reflux under N2
  3. customthe volatiles are removed under vacuum
  4. customNH4OH and flash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH)

Sources & evidence

ORD record
ord-7e86cf4b2efb4677baf3bde41c6d6854
Source dataset
uspto-grants-1991_10
Patent number
US05053338

Reaction notes

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