Sodium Hydroxide → 9-Bromo-1-methyl-1,10-phenanthrolin-2(1H)-one
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]=2Participants
4
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).