Sulfuric Acid → 4-Bromopyridazine-3,6-diol

HRID 595707Notes

Reaction equation

HRID 595707 reaction equation
[NH2:1][NH2:2].OS(O)(=O)=O.[Br:8][C:9]1[C:10](=O)[O:11][C:12](=[O:14])[CH:13]=1>O>[Br:8][C:9]1[C:10](=[O:11])[NH:1][NH:2][C:12](=[O:14])[CH:13]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 9321HydrazineHCID 800273-Bromo-2,5-furandione

Product 1

HCID 2549424-Bromopyridazine-3,6-diolYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of NH2NH2.H2SO4 (362 mg, 2.8 mmol) in H2O (5 mL) was added dropwise 3-bromofuran-2,5-dione (500 mg, 2.8 mmol), and the mixture was stirred at 90° C. for 4 hours. After the reaction, the mixture was filtered to get 4-bromo-1,2-dihydropyridazine-3,6-dione (300 mg, yield: 56%). 1H-NMR (DMSO-d6, 400 MHz) δ 12.47 (s, 1H), 11.17 (s, 1H), 7.62 (s, 1H). MS (M+H)+:191/193.

Workup

  1. customAfter the reaction
  2. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-b9f81f3e3cea4c22acca1559aebe9c92
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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