Hydrazine hydrate (1:1) → 6-Methyl-2,3-dihydro-phthalazine-1,4-dione

HRID 1667518Notes

Reaction equation

HRID 1667518 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[O:6][C:5]2=O.O.[NH2:14][NH2:15]>C(O)(C)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:15][NH:14][C:5]2=[O:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 880694-Methylphthalic anhydride

Product 1

HCID 114579906-Methyl-2,3-dihydro-phthalazine-1,4-dioneYield 72%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5-methyl-isobenzofuran-1,3-dione (6.0 g, 34.1 mmol) and hydrazine hydrate (2.48 mL, 51.1 mmol) in isopropanol (120 mL) was heated at reflux for 4 h. The mixture was allowed to cool and the precipitate was filtered and washed with water (50 mL). The filter cake was dried to afford the title compound (4.32 g, 72%) as a white solid. m/z (M+1)=177.18

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. temperatureto cool
  4. filtrationthe precipitate was filtered
  5. washwashed with water (50 mL)
  6. customThe filter cake was dried

Sources & evidence

ORD record
ord-5f960957ed3d48fe83326da183cf8c4a
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

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