Hydrazine hydrate (1:1) → 5-Aminophthalazine

HRID 2095209Notes

Reaction equation

HRID 2095209 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[N:7][N:8]=[CH:9]2)([O-])=O.O.NN>C(O)C.C1COCC1.[Ni].O>[CH:9]1[C:10]2[C:5](=[C:4]([NH2:1])[CH:13]=[CH:12][CH:11]=2)[CH:6]=[N:7][N:8]=1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 111058745-Nitrophthalazine

Product 1

HCID 112288695-AminophthalazineYield 79%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A reaction vessel was charged with the 5-nitrophthalazine (1.9 g, 10.9 mmol) prepared above, dissolved in a mixture of 60 mL of ethanol:THF (5:1). Hydrazine hydrate (2.5 g, 25 mmol) was added to the reaction mixture followed by a catalytic amount of Raney nickel as a slurry in water. The reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was then passed through a pad of silica gel/celite which was washed with ethanol. The ethanol fractions were combined and evaporated to yield 1.2 g (79%) of the title compound of formula (Z).

Workup

  1. customprepared above,
  2. washwas washed with ethanol
  3. customevaporated

Sources & evidence

ORD record
ord-c27590fc18d44419b149feb7c2228b67
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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