Chlorosuccinimide → 6-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 1521623

Reaktionsgleichung

Reaktionsgleichung von HRID 1521623
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[Cl:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:13])[CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2

Komponenten

4

Edukt 2

HCID 31398ChlorosuccinimideHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 6-bromo-3,4-dihydroquinolin-2(1H)-one (74-3; 20 g, 0.088 mol) in N,N-dimethylformamide (200 mL) was added N-chlorosuccinimide portion wise (17.7 g, 0.132 mol) at 80° C. Reaction mass was allowed to stir at 80° C. for 2 h. The reaction mixture was cooled and diluted with ice cold water. The precipitated solid filtered and dried to obtain title compound. 1H NMR (400 MHz, DMSO-d6) δ: 9.61 (bs, 1H), 7.52-7.51 (d, J=1.6 Hz, 1H), 7.41 (s, 1H), 2.93-2.90 (t, J=8 Hz, 2H). MS (M+1); 261.2.

Aufarbeitung

  1. customReaction mass
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with ice cold water
  4. filtrationThe precipitated solid filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-713904bfce9a416f87c46f5f6ac8d4db
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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