Sodium Azide → HCID 178517318, compound

HRID 133006Notes

Reaction equation

HRID 133006 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][N:7]=[C:8]3[C:13]=2[C:12]=1[C:11](=[O:14])[C:10]1[CH:15]=[CH:16][CH:17]=[CH:18][C:9]3=1.ClC1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C(Cl)=CC=1.[N-:37]=[N+]=[N-].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][N:7]=[C:8]3[C:9]4[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=4[C:11](=[O:14])[NH:37][C:12]=1[C:13]=23

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 41794241,4-DichloroanthraquinoneHCID 11402576HCID 11402576, compound

Product 1

HCID 178517318HCID 178517318, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1.02 g of 5-chloro-2,6-dihydrodibenzo[cd,g]indazol-6-one [synthesized from 1,4-dichloroanthraquinone [CAS No. 602-25-5] as a starting material according to the method described in Patent No. WO-0112609] in 5 ml concentrated sulfuric acid was added 0.78 g of sodium azide [CAS No. 26628-22-8], followed by stirring at room temperature for 2 days. The reaction mixture was poured onto 50 ml of ice-water, the precipitated powder was collected by filtration and dried in vacuo. The powder was dissolved in 10 ml of dimethylformamide and 5 ml of ethyl acetate was added. To the suspension was added saturated aqueous sodium hydrogencarbonate solution, and stirred. The crystals were collected by filtration, sequentially washed with hydrous dimethylformamide and water and dried in vacuo, to give 647 mg of the title compound as green crystals.

Workup

  1. filtrationthe precipitated powder was collected by filtration
  2. customdried in vacuo
  3. dissolutionThe powder was dissolved in 10 ml of dimethylformamide
  4. addition5 ml of ethyl acetate was added
  5. additionTo the suspension was added saturated aqueous sodium hydrogencarbonate solution
  6. stirringstirred
  7. filtrationThe crystals were collected by filtration
  8. washsequentially washed with hydrous dimethylformamide and water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-fb344542f3924f3fb521384b0b1d743c
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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