Methanol → 6-chloro-4-fluoro-8-nitro-9H-beta-carboline

HRID 12236

Reaktionsgleichung

Reaktionsgleichung von HRID 12236
[N+:1]([O-:4])([O-])=[O:2].[Na+].[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([F:20])[C:10]2=1.CO.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[Cl:6][C:7]1[CH:8]=[C:9]2[C:17](=[C:18]([N+:1]([O-:4])=[O:2])[CH:19]=1)[NH:16][C:15]1[CH:14]=[N:13][CH:12]=[C:11]([F:20])[C:10]2=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24268Sodium NitrateHCID 516892Sodium BicarbonateHCID 593375246-Chloro-4-fluoro-9H-beta-carboline

Produkt 1

HCID 671659696-chloro-4-fluoro-8-nitro-9H-beta-carbolineAusbeute 102,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium nitrate (1.5 eq, 53 mmol, 4.5 g) was added portionwise to a solution of Intermediate 65 (1.0 eq, 35 mmol, 7.8 g) in trifluoroacetic acid (200 mL) and the resulting mixture heated at 70° C. for 3 h. After cooling to RT the trifluoroacetic acid was removed on a rotary evaporator to afford a crude solid which was suspended in a small volume of methanol and added dropwise to a vigorously stirred mixture of saturated sodium bicarbonate solution (500 mL). The resulting slurry was stirred for 15 min then the precipitated solids were collected by suction filtration, washed with water (300 mL) and then dried in vacuo to afford 6-chloro-4-fluoro-8-nitro-9H-β-carboline (about 9.5 g) which was used in the subsequent step without further purification.

Aufarbeitung

  1. customwas removed on a rotary evaporator
  2. customto afford a crude solid which
  3. filtrationthe precipitated solids were collected by suction filtration
  4. washwashed with water (300 mL)
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-981b4dc1e0c84bf89a142b850617dd70
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727985B2

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