1,5-Dichloroanthraquinone → HCID 69309607, compound

HRID 2416386Notes

Reaction equation

HRID 2416386 reaction equation
Cl[C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[C:9]([Cl:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.CC[N:21]([CH:25](C)C)C(C)C.[OH2:28].[NH2:29]N>C1COCC1>[Cl:17][C:9]1[CH2:10][C:11](=[O:28])[CH2:12][C:13]2[C:8]=1[CH:7]=[C:6]1[C:15](=[C:2]3[CH:25]=[N:21][N:29]=[C:3]3[CH:4]=[CH:5]1)[CH:14]=2

Participants

5

Reactant 3

HCID 67111,5-DichloroanthraquinoneHCID 24654Hydrazine hydrate (1:1)HCID 81531Diisopropylethylamine

Product 1

HCID 69309607HCID 69309607, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1,5-dichloroanthraquinone (343 mg, 1.2 mmol) and iPr2NEt (240 mg, 1.9 mmol) in THF (5.5 mL) was added hydrazine monohydrate (186 mg, 3.7 mmol) dropwise, and the reaction mixture was heated at reflux for 2 hours. After cooling, the mixture was washed with water and extracted with chloroform. The combined organic layers were washed with brine and dried over MgSO4. Then the residue was separated by column chromatography (silica gel) with chloroform/EtOAc (1/1) as an eluent to give 7-chloropyrazoloanthrone (7) as a brown solid (57 mg, 18%); 1H NMR (DMSO) δ 8.23 (dd, J=7.11, 1.86 Hz, 1H), 7.88-7.82 (m, 2H), 7.78-7.62 (m, 2H), 7.34 (dd, J=7.25, 0.69 Hz, 1H); 13C NMR (DMSO) δ 181.7, 153.7, 137.1, 136.3, 135.5, 134.7, 134.3, 133.0 (2C), 128.6, 126.2, 118.2, 115.2, 110.0.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. washthe mixture was washed with water
  5. extractionextracted with chloroform
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. customThen the residue was separated by column chromatography (silica gel) with chloroform/EtOAc (1/1) as an eluent

Sources & evidence

ORD record
ord-09798de835c54a1f9d8513e797c17ac2
Source dataset
uspto-grants-2004_11
Patent number
US06824998B2

Reaction notes

Loading…