Hydrazine → 2,3,5,6,7,8-Hexahydrophthalazine-1,4-dione

HRID 42220Notes

Reaction equation

HRID 42220 reaction equation
[NH2:1][NH2:2].[C:3]1(=O)[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5](=[O:12])[O:4]1>O.CC(O)=O>[C:5]1(=[O:12])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:3](=[O:4])[NH:2][NH:1]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 124753,4,5,6-Tetrahydrophthalic anhydride

Product 1

HCID 3139202,3,5,6,7,8-Hexahydrophthalazine-1,4-dioneYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of hydrazine (392 μL, 13.1 mmol) in water (6 mL) and HOAc (2 mL) is added 4,5,6,7-tetrahydro-isobenzofuran-1,3-dione (2 g, 13.1 mmol). The reaction mixture is refluxed for 3 h, then cooled down to room temperature and the precipitate is collected by filtration, washed with water and dried under vacuum oven to give 2,3,5,6,7,8-hexahydro-phthalazin-1,4-dione (compound 10d) (2.09 g, 95.7%). m/z=167.05 [M+1]

Workup

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. filtrationthe precipitate is collected by filtration
  3. washwashed with water
  4. customdried under vacuum oven

Sources & evidence

ORD record
ord-7b0fbd207cde447f8088afb97737bb35
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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