8-Nitroquinoline → 8-Nitroquinolin-7-amine

HRID 1615633Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615633
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[I-].C[N+:16](C)(C)N.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O>[N+:1]([C:4]1[C:5]([NH2:16])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 118308-NitroquinolineHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 129549938-Nitroquinolin-7-amineAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 8-nitroquinoline (1.88 g, 10 mmol) and 1,1,1-trimethylhydrazinium iodide (3.03 g, 15 mmol) in anhydrous dimethyl sulfoxide (DMSO) (20 mL) was added potassium tert-butoxide (3.36 g, 30 mmol) as a solid. The mixture was stirred at room temperature for 1 h. The mixture was then poured into saturated aqueous ammonium chloride and extracted with EtOAc. The organic layers were concentrated and the residue was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give 8-nitroquinolin-7-amine as a yellow solid (300 mg, yield 18%). ESI MS: m/z 189 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.93 (dd, 1H, 3.2 Hz, 2J=1.6 Hz), 8.00 (dd, 1H, 1J=6.4 Hz, 2J=1.6 Hz), 7.69 (d, 1H, J=6.8 Hz), 7.29 (dd, 1H, 1J=6.0 Hz, 2J=3.2 Hz), 7.00 (d, 1H, J=7.2 Hz), 5.60 (s, 2H).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. concentrationThe organic layers were concentrated
  3. customthe residue was purified by silica gel column chromatography (
  4. washeluting with PE/EtOAc v/v 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-88d6db43994f4182a9107cdef90ee653
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765760B2

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