Iodine → HCID 20141777, Verbindung

HRID 649539

Reaktionsgleichung

Reaktionsgleichung von HRID 649539
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH:6]=[CH:5]2.[C:14]([C:17]1[N:18]=[C:19]([CH3:22])[NH:20][CH:21]=1)(=[O:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].II.BrC1C(=O)NC2C(C=1)=CC=CC=2>CN1CCCC1=O.ClCCl.CO>[C:14]([C:17]1[N:18]=[C:19]([CH3:22])[N:20]([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([CH3:12])[CH:11]=2)[NH:8][C:7](=[O:13])[CH:6]=[CH:5]3)[CH:21]=1)(=[O:16])[CH3:15]

Komponenten

9

Edukt 5

HCID 807IodineHCID 11430Potassium CarbonateHCID 2683383-Bromoquinolin-2-olHCID 138361836-Bromo-8-methylquinolin-2(1H)-oneHCID 178467223HCID 178467223, Verbindung

Produkt 1

HCID 20141777HCID 20141777, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-8-methyl-2-(1H)-quinolone (2.38 g), (see Preparation 67 of European patent application publication No. 0148623), 4-acetyl-2-methylimidazole (2.48 g), finely divided copper-bronze (0.64 g), potassium carbonate (1.38 g), and a few crystals of iodine was stirred and heated in N-methyl-2-pyrrolidone (8 cm3) at 190° C. for 24 hours under nitrogen. The cooled mixture was then poured into methanol:dichloromethane (100 cm3, 1:10 by volume), stirred and filtered. The filtrate was poured into aqueous ammonia (20 cm3, S.G. 0.880) and the mixture was filtered through "Solkafloc" (Trademark for a cellulose-based filtering aid). The filtrate was separated and the aqueous phase was re-extracted with methanol:dichloromethane (3×100 cm3), 1:10 by volume). The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trademark]). Elution with methanol:dichloromethane, 1:33 by volume, followed by combination and evaporation of the appropriate fractions, gave unreacted starting bromo-quinolone (0.68 g) and a solid which was recrystallised from ethyl acetate/methanol to afford the title compound, m.p. 306°-8°, (0.26 g), which was also confirmed spectroscopically to be identical to the product of Example 3.

Aufarbeitung

  1. customPreparation 67 of European patent application publication No
  2. filtrationfiltered
  3. additionThe filtrate was poured into aqueous ammonia (20 cm3, S.G. 0.880)
  4. filtrationthe mixture was filtered through "Solkafloc" (Trademark for a cellulose-
  5. filtrationbased filtering aid)
  6. customThe filtrate was separated
  7. extractionthe aqueous phase was re-extracted with methanol
  8. dry with materialdried (MgSO4) organic extracts
  9. customwere evaporated in vacuo
  10. customto give a residue which
  11. customwas chromatographed on silica (Merck "MK 60.9385" [Trademark])
  12. washElution with methanol
  13. customdichloromethane, 1:33 by volume, followed by combination and evaporation of the appropriate fractions
  14. customgave unreacted
  15. customa solid which was recrystallised from ethyl acetate/methanol

Quellen und Nachweise

ORD-Eintrag
ord-fd88753c7fe748388fa3e1e6d2493b12
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04740513

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