Tetrahydrofuran → HCID 178517114, compound

HRID 133005Notes

Reaction equation

HRID 133005 reaction equation
[N:1]1[NH:2][C:3]2[CH:17]=[CH:16][CH:15]=[C:5]3[C:6](=[O:14])[C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=1[C:4]=23.[N-:18]=[N+]=[N-].[Na+].C(OCC)(=O)C.O1CCCC1>S(=O)(=O)(O)O>[N:1]1[NH:2][C:3]2[CH:17]=[CH:16][CH:15]=[C:5]3[C:6](=[O:14])[NH:18][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=1[C:4]=23

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8515Anthra(1,9-cd)pyrazol-6(2H)-oneHCID 8857Ethyl AcetateHCID 33557Sodium Azide

Product 1

HCID 178517114HCID 178517114, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 100 mg of 2,6-dihydrodibenzo[cd,g]indazol-6-one [CAS No. 129-56-6] in 0.6 ml concentrated sulfuric acid was added 78 mg of sodium azide [CAS No. 26628-22-8], followed by stirring at room temperature for 3 days. After adding ice, the reaction mixture was poured into a mixture solution of 100 ml of ethyl acetate and 10 ml of tetrahydrofuran and washed with saturated sodium hydrogen carbonate solution. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was dissolved in tetrahydrofuran, adsorbed by 3.5 g of silica gel and subjected to silica gel chromatography [Wako Gel C-200, 2 g]. The fractions of tetrahydrofuran-toluene [19:1 to 9:1] were concentrated, and the resulting powder was suspended in tetrahydrofuran-toluene. A powder was collected by filtration, and recrystallized from dimethylformamide-water, to give 27 mg of 6,7-dihydro-2H-benzo[6,7]azepino[5,4,3-cd]indazol-6-one as green needles.

Workup

  1. additionAfter adding ice
  2. washwashed with saturated sodium hydrogen carbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in tetrahydrofuran
  7. concentrationThe fractions of tetrahydrofuran-toluene [19:1 to 9:1] were concentrated
  8. filtrationA powder was collected by filtration
  9. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-a7299b688e6945bd80f75dc9229363ba
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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