Cyanogen Bromide → HCID 68571396, Verbindung

HRID 655266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655266
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]([NH:15][NH2:16])=[O:14])=[CH:7][CH:6]=2.[N:17]#[C:18]Br>CO.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]1[O:14][C:18]([NH2:17])=[N:16][N:15]=1)=[CH:7][CH:6]=2

Komponenten

5

Edukt 2

HCID 10476Cyanogen BromideHCID 57742331HCID 57742331, Verbindung

Produkt 1

HCID 68571396HCID 68571396, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (3-bromo-quinolin-6-yl)-acetic acid hydrazide (prepared according to procedure described herein) (4.12 g, 14.7 mmol), cyanogen bromide (1.1 eq., 16.2 mmol, 1.7 g) and KHCO3 (1.25 eq., 18.3 mmol, 1.83 g) was stirred in methanol (30 mL) at ambient temperature for 18 hours. The was then diluted with water (40 mL) and the solid was collected via filtration and washed with cold methanol and dried to return the title compound as an off white solid (4.02 g, 13.2 mmol, 90%). 1H NMR (DMSO-d6): δ 4.27 (2H, s), 6.94 (s, 2H), 7.71 (dd, 1H), 7.86 (d, 1H), 8.02 (d, 1H), 8.73 (d, 1H); 8.93 (d, 1H); MS (m/z) 305 [M+H+]+.

Aufarbeitung

  1. filtrationthe solid was collected via filtration
  2. washwashed with cold methanol
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b6dd3c3860b64c2580cd3720479d9329
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071581B2

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