Sodium Hydroxide → 9-Bromo-1-methyl-1,10-phenanthrolin-2(1H)-one

HRID 241399

Reaktionsgleichung

Reaktionsgleichung von HRID 241399
S([O-])(O)(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:19]([N:20]=1)=[C:18]1[C:13]([CH:14]=[CH:15][CH:16]=[N+:17]1[CH3:21])=[CH:12][CH:11]=2.[OH-:22].[Na+]>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[C:19]([N:20]=1)=[C:18]1[C:13]([CH:14]=[CH:15][C:16](=[O:22])[N:17]1[CH3:21])=[CH:12][CH:11]=2

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 866711159-Bromo-1-methyl-1,10-phenanthrolinium hydrogen sulfate

Produkt 1

HCID 713604359-Bromo-1-methyl-1,10-phenanthrolin-2(1H)-oneAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178511488HCID 178511488, VerbindungKatalysator

Versuchsvorschrift

To a stirred aqueous solution of potassium ferricyanide (100 g; 303 mmol) (1.1 L), compound (8) (42.7 g; 115 mmol) and an aqueous sodium hydroxide (76 g; 1.9 mol) (110 mL) were alternately added over 25 minutes in an ice bath (inner temperature of 4 to 6° C.). The resulting mixture was stirred in an ice bath for 1 hour, and further stirred at room temperature for 3.5 hours. Crude crystals which precipitated out were separated by filtration and washed with water, and then dried. The resulting crude crystals were separated and purified by silica gel column chromatography (SiO2 800 g) (chloroform/methanol=50/1 to 30/1 to 20/1) and dried to give 27.4 g (yield: 82%) of the title compound (9).

Aufarbeitung

  1. stirringfurther stirred at room temperature for 3.5 hours
  2. customCrude crystals which precipitated out
  3. customwere separated by filtration
  4. washwashed with water
  5. customdried
  6. customThe resulting crude crystals were separated
  7. custompurified by silica gel column chromatography (SiO2 800 g) (chloroform/methanol=50/1 to 30/1 to 20/1)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-85de17c10c2547bc8d85c7f2b1942eab
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648194B2

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