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

HRID 241399

Reaction equation

HRID 241399 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 713604359-Bromo-1-methyl-1,10-phenanthrolin-2(1H)-oneYield 82.4%

Reagents, catalysts & solvents 1

HCID 178511488HCID 178511488, compoundCatalyst

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-85de17c10c2547bc8d85c7f2b1942eab
Source dataset
uspto-grants-2014_02
Patent number
US08648194B2

Linked notes

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