Methanol → N-butyl-8-nitro-2-quinoline amine

HRID 886773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 886773
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.CO.C(OCC)C.[CH2:22]([NH2:26])[CH2:23][CH2:24][CH3:25]>>[CH2:22]([NH:26][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:23][CH2:24][CH3:25]

Komponenten

5

Edukt 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 8007ButylamineHCID 3194532-Chloro-8-nitroquinoline

Produkt 1

HCID 67057974N-butyl-8-nitro-2-quinoline amineAusbeute 90 %

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

2-chloro-8-nitroquinoline (0.20 g; 0.96 mmol) is suspended in 9.5 ml of 1-butylamine and the medium is heated under reflux (78° C.) for 15 hours. The yellow solution obtained is subsequently concentrated under vacuum. The crude reaction product is taken up in a minimum volume of CH3OH and poured over 3 ml of diethyl ether. After centrifugation, butyl ammonium chloride crystals are removed and the supernatant is concentrated under reduced pressure to yield N-butyl-8-nitro-2-quinoline amine in the form of a yellow oil (0.21 g; 0.86 mmol, yield=90%). NMR-1H (250 MHz, CDCl3) δ, ppm: 7.83 (dd, 3J (H, H)=7.5 Hz, 4J (H, H)=1.5 Hz, 1H); 7.77 (d, 3J (H, H)=9.0 Hz, 1H); 7.69 (dd, 3J (H, H)=8.0 Hz, 4J (H, H)=1.5 Hz, 1H); 7.14 (m, 1H), 6.67 (d, 3J (H, H)=9.0 Hz, 1H); 5.07 (s large, 1H); 3.47 (m, 2H); 1.60 (m, 2H); 1.39 (m, 2H); 0.93 (t, 3J (H, H)=7.5 Hz, 3H). NMR-13C (63 MHz, CDCl3) δ, ppm: 157.8 (Cq); 145.6 (Cq); 140.2 (Cq); 136.7 (CH); 131.5 (CH); 124.7 (CH); 124.1 (CH); 119.7 (CH); 113.3 (Cq); 41.3 (CH2); 31.5 (CH2); 20.2 (CH2); 13.8 (CH3). MS (CID, NH3): m/z=246 (MH+). Analysis (%) for C13H15N3O2: calculated C, 63.66. H, 6.16. N, 17.13. found C, 63.33. H, 6.21. N, 16.64.

Aufarbeitung

  1. temperaturethe medium is heated
  2. customThe yellow solution obtained
  3. concentrationis subsequently concentrated under vacuum
  4. customThe crude reaction product
  5. customAfter centrifugation, butyl ammonium chloride crystals are removed
  6. concentrationthe supernatant is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1020db7c39b34c708a37b43cd92d62f4
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247396B2

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