Hydrazine hydrate (1:1) → 4-(3-Chlorophenyl)pyridazine-3,6-diol

HRID 2239888Notes

Reaction equation

HRID 2239888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=O)[O:10][C:11](=[O:13])[CH:12]=2)[CH:5]=[CH:6][CH:7]=1.O.[NH2:16][NH2:17]>O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([OH:13])[N:17]=[N:16][C:9]=2[OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86618521HCID 86618521, compound

Product 1

HCID 1785155844-(3-Chlorophenyl)pyridazine-3,6-diol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a 25 mL flask was added 3-(3-chlorophenyl)furan-2,5-dione (1.7 g, 8.15 mmol) from (1a) and hydrazine hydrate (0.476 mL, 9.78 mmol) in water (6 mL) and acetic acid (4 mL). The resulting mixture was refluxed for 18 hours. The solution was cooled and placed in the refrigerator for 1 hour. The resulting precipitate was filtered and dried, then purified by flash chromatography eluting with 5% methanol/dichloromethane to give 4-(3-chlorophenyl)pyridazine-3,6-diol.

Workup

  1. temperatureThe resulting mixture was refluxed for 18 hours
  2. temperatureThe solution was cooled
  3. filtrationThe resulting precipitate was filtered
  4. customdried
  5. custompurified by flash chromatography
  6. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-a2a103fb8fb34b94a6d33ca5cde93a59
Source dataset
uspto-grants-2010_05
Patent number
US07723336B2

Reaction notes

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