Potassium Carbonate → HCID 178513408, compound

HRID 1710099

Reaction equation

HRID 1710099 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]#[N:20])=[N:11]1>C(O)C.CO>[CH:15]1[CH:14]=[C:13]2[C:12]([NH:11][NH:10][C:18]2=[CH:17][CH:16]=1)=[C:19]([N:2]=[O:3])[NH2:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4375561H-Indazole-3-carbonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178513408HCID 178513408, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Hydroxylamine hydrochloride (1.5 g) and potassium carbonate (3.83 g) were stirred together in absolute ethanol (100 ml) for 15 minutes. Indazole-3-carbonitrile (2 g) was added and the solution heated at reflux for 4 hours, cooled to room temperature and diluted with methanol (5 ml). The solution was filtered and the solvent evaporated. The residue was extracted with anhydrous ether, the extracts were dried over MgSO4, filtered and the solvent removed to afford a white solid, which was recrystallised from acetone/dichloromethane to afford the title compound (900 mg), m.p. 155°-158° C. δH (360 MHz, CDCl3) 6.46 (1H, brm, N-OH), 7.17 (1H, t, J=1 Hz, H-6), 7.41 (1H, t, J=2 Hz, H-5), 7.55 (1H, d, J=2 Hz, H-4), 8.03 (1H, t, J=2 Hz, H-7); m/z (M+ , 100%), 176 (100), 144 (80), 119 (25), 92 (15).

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 4 hours
  3. filtrationThe solution was filtered
  4. customthe solvent evaporated
  5. extractionThe residue was extracted with anhydrous ether
  6. dry with materialthe extracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto afford a white solid, which
  10. customwas recrystallised from acetone/dichloromethane

Sources & evidence

ORD record
ord-53e1ec03f4654b81a1784050e8a75879
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Linked notes

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