Sodium Cyanide → 1-Acetylindoline-5-carbonitrile

HRID 219570

Reaktionsgleichung

Reaktionsgleichung von HRID 219570
N[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:13])[CH3:12])[CH2:6][CH2:5]2.N([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[C-]#N.[Na+].[Cu](C#N)[C:28]#[N:29]>Cl.O>[C:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:28]#[N:29])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)(=[O:13])[CH3:12]

Komponenten

8

Edukt 5

HCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 2925071-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-oneHCID 23668193Sodium NitriteHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 185264211-Acetylindoline-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(5-aminoindolin-1-yl)ethanone (Aldrich, 865 mg; 4.91 mmol) in HCl (2.1 M, 2.95 mL) was treated with sodium nitrite (358 mg; 5.18 mmol) and the mixture was stirred at 0° C. for 3 hours. The solution was neutralized with sodium carbonate (3.12 g; 29.43 mmol) and the resulting mixture was added to a suspension of sodium cyanide (519 mg; 10.6 mmol) and copper cyanide (467 mg; 5.21 mmol) in water (4 mL) at 0° C. The resulting suspension was heated to 50° C., stirred for 30 minutes, cooled to 0° C. and the precipitated solid was collected by filtration. The collected solid was recrystallised from aqueous acetonitrile to give the title compound as a brown solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.16 (1H, d, J=8.3 Hz), 7.72-7.62 (2H, m), 4.23-4.11 (2H, m), 2.54 (3H, t, J=2.1 Hz), 2.23 (3H, s).

Aufarbeitung

  1. temperatureThe resulting suspension was heated to 50° C.
  2. stirringstirred for 30 minutes
  3. temperaturecooled to 0° C.
  4. filtrationthe precipitated solid was collected by filtration
  5. customThe collected solid was recrystallised from aqueous acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-b28b7cd070a24ba7a77dec55ee01e3f8
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202856B2

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