2-Chloroanthraquinone → Anthra(1,9-cd)pyrazol-6(2H)-one

HRID 1243631Notes

Reaction equation

HRID 1243631 reaction equation
[NH2:1][NH2:2].Cl[C:4]1[CH:17]=[CH:16][C:15]2[C:14](=[O:18])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]=2[CH:5]=1>N1C=CC=CC=1>[N:1]1[NH:2][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[C:7]=1[C:6]1[C:15]([C:14]3=[O:18])=[CH:16][CH:17]=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 85532-ChloroanthraquinoneHCID 9321Hydrazine

Product 1

HCID 8515Anthra(1,9-cd)pyrazol-6(2H)-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Anhydrous hydrazine is added to a solution of 2-chloroanthraquinone (Aldrich) in 10 mL pyridine, and the mixture heated at 100° C. for 16 hours. The mixture is cooled and the solvent is evaporated in vacuo. The residue is taken in hot 6N HCl, and the solid is collected by filtration. Flash chromatography of the crude material on silica gel affords anthra[1,9cd]pyrazol-6(2H)-one (“Compound 1”) as yellow solids.

Workup

  1. temperatureThe mixture is cooled
  2. customthe solvent is evaporated in vacuo
  3. filtrationthe solid is collected by filtration

Sources & evidence

ORD record
ord-8ceaabfd945f4a2c803c758b0b7b6b4e
Source dataset
uspto-grants-2006_10
Patent number
US07119114B1

Reaction notes

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