Hydrazine → 5-hydroxy-2,3-dihydrophthalazine-1,4-dione

HRID 741534Notes

Reaction equation

HRID 741534 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=O)[C:3]=12)=[O:6].[NH2:13][NH2:14]>C(O)(=O)C>[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:3]=1[C:8](=[O:7])[NH:13][NH:14][C:5]2=[O:6]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 965803-Hydroxyphthalic anhydride

Product 1

HCID 53709685-hydroxy-2,3-dihydrophthalazine-1,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Hydroxyphthalic anhydride (2.0 g, 12.2 mmol, Aldrich) was stirred with 25 mL of glacial acetic acid until nearly all dissolved. Hydrazine (8.4 mL, 268 mmol) was added dropwise to the mixture. The reaction mixture fumed and became homogeneous with development of a yellow color. After a few minutes, a white precipitate formed and the yellow color faded. The mixture was stirred for three days and then filtered. The solids were washed with 150 mL of water followed by 125 mL of acetonitrile and allowed to dry in the air and then under vacuum. Yield: 2.06 g (95%). 1H NMR (DMSO-d6): δ 12.83 (s, 1H), 12.06 (s, 1H), 11.68 (s, 1H), 7.76-7.70 (t, 1H), 7.34-7.31 (d, 1H), 7.14-7.12 (d, 1H); 13C NMR (DMSO-d6): δ 163.04, 160.68, 152.74, 136.37, 126.38, 118.34, 114.50, 113.76; MS: (m/e) 178 (M+), 148, 120, 92.

Workup

  1. waitAfter a few minutes
  2. customa white precipitate formed
  3. filtrationfiltered
  4. washThe solids were washed with 150 mL of water
  5. customto dry in the air

Sources & evidence

ORD record
ord-af01db63257f4f64b801d1c480a2a5e2
Source dataset
uspto-grants-1996_09
Patent number
US05552298

Reaction notes

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