Potassium Carbonate → HCID 178513408, compound

HRID 2248599Notes

Reaction equation

HRID 2248599 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 extraced with anhydrous either, 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 (1 H, brm, N--OH), 7.17 (1 H, t, J=1 Hz, H-6), 7.41 (1 H, t, J=2 Hz, H-5), 7.55 (1 H, d, J=2 Hz, H-4), 8.03 (1 H, 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. dry with materialwere dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customto afford a white solid, which
  9. customwas recrystallised from acetone/dichloromethane

Sources & evidence

ORD record
ord-9bed6f6cf5c74088ad936fe2ac13aee6
Source dataset
uspto-grants-1991_08
Patent number
US05041456

Reaction notes

Loading…