Réaction #84069

ord-3b909b9459f547ddaf88c07c65870078

Équation de réaction

N#Cc1ccc(-c2ccc3cc(O)ccc3n2)cc1
4-(6-hydroxyquinolin-2-yl)benzonitrile
Cl.NO
NH2OH.HCl
N=C(NO)c1ccc(-c2ccc3cc(O)ccc3n2)cc1
desired product
Rendement 78.0%
N=C(NO)c1ccc(-c2ccc3cc(O)ccc3n2)cc1
N-hydroxy-4-(6-hydroxyquinolin-2-yl)benzimidamide
Rendement 78.0%

Solvants

Conditions de réaction

Température
80°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Concentrationfollowed by concentration in vacuo
  2. 2
    workup.STIRRINGstirred for 1 hour
  3. 3
    FiltrationFiltration
  4. 4
    Autredrying of the solids

Mode opératoire

See Scheme 4, route B. 4-(6-hydroxyquinolin-2-yl)benzonitrile (900 mg, 3.68 mmol) was dissolved in 25 mL of EtOH and to it was added NH2OH.HCl (500 mg, 7.36 mmol) and TEA (1.5 mL). The mixture was stirred at 80° C. for 2 hours followed by concentration in vacuo. The crude solids were then suspended in 25 mL of H2O and stirred for 1 hour. Filtration and drying of the solids yielded desired product (800 mg, 78% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09433618B2uspto-grants-2016_09