1-(Methylsulphonyl)acetone → 6-Bromo-3-methanesulfonyl-2-methyl-4-phenyl-quinoline

HRID 13655

Reaktionsgleichung

Reaktionsgleichung von HRID 13655
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.[CH3:17][S:18]([CH2:21][C:22](=O)[CH3:23])(=[O:20])=[O:19].[Na]>CC(O)C>[Br:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:22]([CH3:23])[C:21]([S:18]([CH3:17])(=[O:20])=[O:19])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 786951-(Methylsulphonyl)acetoneHCID 996772-Amino-5-bromobenzophenoneHCID 5360545Sodium

Produkt 1

HCID 120016266-Bromo-3-methanesulfonyl-2-methyl-4-phenyl-quinolineAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

(2-Amino-5-bromo-phenyl)-phenyl-methanone (10 g, 36 mmol), methanesulfonylacetone (7.4 g, 54 mmol) and sodium tetrachloroaureate(III) dihydrate (720 mg, 1.8 mmol) were heated at reflux in 2-propanol (100 mL) for 4.5 days. The resulting suspension was evaporated to dryness and the residue extracted with dichloromethane (2×), 1 N NaOH (2×), which removes excess of methanesulfonylacetone, and sat. NaCl (1×). The crude product was purified twice by chromatography in dichloromethane and then crystallized from dichloromethane/heptane by evaporation of dichloromethane. One obtained 4.6 g (33%) of beige crystals. MS: m/z=375/377 (M).

Aufarbeitung

  1. customThe resulting suspension was evaporated to dryness
  2. extractionthe residue extracted with dichloromethane (2×), 1 N NaOH (2×), which
  3. customremoves excess of methanesulfonylacetone, and sat. NaCl (1×)
  4. customThe crude product was purified twice by chromatography in dichloromethane
  5. customcrystallized from dichloromethane/heptane by evaporation of dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e1894e98006d45e997e4443d44c97654
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728142B2

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