Sodium Hydroxide → 1-Methyl-1,10-phenanthrolin-2(1H)-one

HRID 716552Notes

Reaction equation

HRID 716552 reaction equation
[I-].[CH3:2][N+:3]1[C:16]2[C:7](=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]=[CH:13][CH:12]=[CH:11]3)[CH:6]=[CH:5][CH:4]=1.[OH-:17].[Na+]>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[CH3:2][N:3]1[C:16]2[C:7](=[CH:8][CH:9]=[C:10]3[C:15]=2[N:14]=[CH:13][CH:12]=[CH:11]3)[CH:6]=[CH:5][C:4]1=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117716101-Methyl-1,10-phenanthrolinium iodide

Product 1

HCID 35813871-Methyl-1,10-phenanthrolin-2(1H)-oneYield 96.4%

Reagents, catalysts & solvents 1

HCID 178511488HCID 178511488, compoundCatalyst

Procedure

To a stirred aqueous solution of potassium ferricyanide (92.2 g; 280 mmol) (1.12 L), compound (1) (37.6 g; 117 mmol) and an aqueous solution of sodium hydroxide (69.3 g; 1.73 mol) (200 mL) were alternately added in an ice bath (inner temperature of 10 to 15° C.) over 20 minutes. The resulting reaction mixture was stirred at room temperature for 3 hours. Crude crystals which precipitated out were filtered out and dried. The resulting crude crystals were dissolved in toluene (1.1 L) and benzene (450 mL), and insoluble matters were filtrated out. The filtrate was evaporated under reduced pressure, and the resulting residue was washed with isopropyl ether and ethyl acetate, and then dried to give 23.7 g (yield: 75%) of the title compound (2).

Workup

  1. customThe resulting reaction mixture
  2. customCrude crystals which precipitated out
  3. filtrationwere filtered out
  4. customdried
  5. dissolutionThe resulting crude crystals were dissolved in toluene (1.1 L)
  6. filtrationbenzene (450 mL), and insoluble matters were filtrated out
  7. customThe filtrate was evaporated under reduced pressure
  8. washthe resulting residue was washed with isopropyl ether and ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-fccf4c88515e4aafb5c7bc1033719594
Source dataset
uspto-grants-2015_11
Patent number
US09187690B2

Reaction notes

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