N-bromobutanimide → 6-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

HRID 1521671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521671
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:13][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Produkt 1

HCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (157-2; 8.30 g, 50.10 mmol) in N,N-dimethylformamide (250 mL) was added N-bromosuccinimide (9.80 g, 55.10 mmol) in N,N-dimethylformamide (120 mL) at 0° C. Reaction mixture was allowed to stir at room temperature for 18 h, then cooled and diluted with ice cold water (500 mL). The resulting precipitated was filtered and dried to obtain title compound (white solid). 1H NMR (DMSO-D6, 500 MHz) 6=10.20 (s, 1H), 7.37 (dd, J=2.0 Hz, JHF=10.0 Hz, 1H), 7.26 (s, 1H), 2.93 (t, J=7.0 Hz, 2H), 2.47 (t, J=7.5 Hz, 2H).

Aufarbeitung

  1. customReaction mixture
  2. temperaturecooled
  3. customThe resulting precipitated
  4. filtrationwas filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d954e5f298b14c0b87995107325d6721
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

Notizen zur Reaktion

Wird geladen…