Methyl iodide → 8-fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-one

HRID 1991324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1991324
[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.I[CH3:17]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:17])[C:9](=[O:12])[CH2:8][CH2:7]2

Komponenten

5

Edukt 2

HCID 6328Methyl iodideHCID 21877762HCID 21877762, Verbindung

Produkt 1

HCID 218779148-fluoro-1-methyl-6-nitro-3,4-dihydro-1H-quinolin-2-oneAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

8-Fluoro-6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 1, 3.13 g, 0.0149 mol) and iodomethane (1.39 ml, 0.0223 mol) in DMF (25 ml) are stirred at room temperature overnight. The reaction is diluted with water and the resulting precipitate collected by filtration, washed well with water, and dried under vacuum to give the title compound as an orange solid (2.97 g, 89%); 1H NMR (300 MHz, CDCl3) δ 2.56-2.61 (m, 2H), 2.99-3.04 (m, 2H), 3.32 (s, 3H), overlapping 8.06 (s, 1H) and 8.08 (dd, 1H); [M+H]+=225.

Aufarbeitung

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed well with water
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f70a806d72374d16a5c84be92bb878ba
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645781B2

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