6-bromo-2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dione → 2-Hydroxy-6-methylthio-benzo[de]isoquinoline-1,3-dione

HRID 567006

Reaktionsgleichung

Reaktionsgleichung von HRID 567006
[CH3:1][S-:2].[Na+].Br[C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:20])[N:10]([OH:19])[C:11](=[O:18])[C:12]3[C:17]=2[C:16]=1[CH:15]=[CH:14][CH:13]=3>C(O)C>[OH:19][N:10]1[C:9](=[O:20])[C:8]2[CH:7]=[CH:6][C:5]([S:2][CH3:1])=[C:16]3[C:17]=2[C:12](=[CH:13][CH:14]=[CH:15]3)[C:11]1=[O:18]

Komponenten

4

Edukt 2

HCID 7084296-bromo-2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dioneHCID 4378561Sodium methanethiolate

Produkt 1

HCID 226239682-Hydroxy-6-methylthio-benzo[de]isoquinoline-1,3-dioneAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium thiomethoxide (0.9 g, 12.0 mmol) was added to a solution of 6-bromo-2-hydroxy-benzo[de]isoquinoline-1,3-dione (1.2 g, 4.0 mmol, from Example 4) in ethanol (200 mL). The mixture was refluxed for 48 hours and concentrated. The solid residue was dissolved in water and acidified with concentrated HCl to pH 4. The resulting precipitate was filtered, washed with water, and dried to give 0.8 g of the title compound, mp 301-206° C.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 48 hours
  2. concentrationconcentrated
  3. dissolutionThe solid residue was dissolved in water
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-845f56130ab94909b2c759e7ba29dc8b
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06177423B1

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