Reaktion #40499

ord-6c4fa2e590f5443b9ababf7aea0a81bf

Reaktionsgleichung

Cc1cncc2[nH]c3ccccc3c12
4-methyl-9H-β-carboline
O=C1CCC(=O)N1Cl
NCS
O=C([O-])O.[Na+]
sodium bicarbonate
Cc1cncc2[nH]c3ccc(Cl)cc3c12
6-chloro-4-methyl-9H-β-carboline
Ausbeute 93.7%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGthe reaction mixture was stirred for 5 hr
  2. 2
    Extraktionthe reaction mixture was extracted twice with EtOAc (100 ml)
  3. 3
    WaschenThe combined organic layers were washed with brine
  4. 4
    Trocknendried over MgSO4
  5. 5
    Filtrationfiltered
  6. 6
    Einengenconcentrated

Vorschrift

4-methyl-9H-β-carboline (97 mg, 0.532 mmol) was dissolved in HCl (1N, 4 ml) and stirred at RT. NCS (85 mg, 0.637 mmol) was added thereto and the reaction mixture was stirred for 5 hr. Saturated sodium bicarbonate solution (20 ml) was added thereto and the reaction mixture was extracted twice with EtOAc (100 ml). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give 6-chloro-4-methyl-9H-β-carboline (108 mg) as an oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727985B2uspto-grants-2010_06