Hydrazine hydrate (1:1) → 6-Bromophthalazine-1,4-diol

HRID 1803508Notes

Reaction equation

HRID 1803508 reaction equation
[Br: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>[Br: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 665904-Bromophthalic anhydride

Product 1

HCID 113794786-Bromophthalazine-1,4-diolYield 72.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5-Bromo-isobenzofuran-1,3-dione (6.0 g, 26.4 mmol) and hydrazine hydrate (1.51 mL, 32.4 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 (4.6 g, 72.3%) as a white solid. m/z (M+1)=241.05

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-3bc26c82643b4332ad27166729f472f2
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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