Sodium Bicarbonate → 6-Chloro-7-methoxy-9h-pyrido[3,4-b]indol-8-amine

HRID 552175

Reaktionsgleichung

Reaktionsgleichung von HRID 552175
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:17]([O-])=O)[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[H][H].C([O-])(O)=O.[Na+]>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:17])[C:14]=1[O:15][CH3:16])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 593375346-chloro-7-methoxy-8-nitro-9H-pyrido[3,4-b]indoleHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 213627436-Chloro-7-methoxy-9h-pyrido[3,4-b]indol-8-amineAusbeute 112,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

6-chloro-7-methoxy-8-nitro-9H-β-carboline (510 mg, 1.84 mmol) was suspended in 50 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 (15 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 product (512 mg, quantitative yield). 1H-NMR (300 MHz, methanol-d4): 63.90 (s, 3H), 7.63 (s, 1H), 8.11 (d, 1H), 8.27 (d, 1H), 8.84 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.12 min.

Aufarbeitung

  1. filtrationUpon filtration
  2. customthrough a pad of celite and evaporation of the methanol
  3. customa dark brown solid was obtained
  4. customThe light brown solid that precipitated out
  5. filtrationwas collected by filtration
  6. customdried thoroughly in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8dc65b6babc14e4e83b0008d187fd1c9
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951801B2

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