Réaction #40473

ord-f36f8b53201943fe85c6b7396fde7d0e

Équation de réaction

O=[N+]([O-])c1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12
6-chloro-7-cyclopropylmethoxy-8-nitro-9H-β-carboline
[H][H]
hydrogen
O=C([O-])O.[Na+]
NaHCO3
Nc1c(OCC2CC2)c(Cl)cc2c1[nH]c1cnccc12
6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine
Rendement 80.1%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    FiltrationUpon filtration
  2. 2
    Autrethrough a pad of celite and evaporation of the methanol
  3. 3
    Autrea dark brown solid was obtained
  4. 4
    AutreThe light brown solid that precipitated out
  5. 5
    Filtrationwas collected by filtration
  6. 6
    Autredried thoroughly in vacuo

Mode opératoire

6-chloro-7-cyclopropylmethoxy-8-nitro-9H-β-carboline (510 mg, 1.61 mmol) was suspended in 12 ml of methanol and 100 mg of Pd/C(10%) was added. The flask was fitted with a balloon of hydrogen and the reaction mixture was stirred overnight at RT. Upon filtration through a pad of celite and evaporation of the methanol, a dark brown solid was obtained. This residue was suspended in methanol (10 ml) and added, with vigorous stirring, to a solution of saturated NaHCO3 (100 ml). The light brown solid that precipitated out was collected by filtration and dried thoroughly in vacuo to give the desired 6-chloro-7-cyclopropylmethoxy-9H-β-carbolin-8-ylamine (371 mgs, 80% yield).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07727985B2uspto-grants-2010_06