1,10-Phenanthroline → 1-Methyl-1,10-phenanthrolinium iodide

HRID 716551Notes

Reaction equation

HRID 716551 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[CH3:15][I:16]>[N+](C1C=CC=CC=1)([O-])=O>[I-:16].[CH3:15][N+:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 13181,10-PhenanthrolineHCID 6328Methyl iodide

Product 1

HCID 117716101-Methyl-1,10-phenanthrolinium iodideYield 88%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

Under a stream of argon, 1,10-phenanthroline (23 g; 127 mmol) was dissolved in nitrobenzene (500 mL). To the reaction mixture, methyl iodide (45.29 g; 319 mmol) was 35° C. for 24 hours. The reaction mixture was cooled in an ice bath, filtered out. The resulting solids were sequentially washed with nitrobenzene, benzene, and ethanol, and evaporated under reduced pressure to give 36 g (yield: 88%) of the title compound (1).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationfiltered out
  3. washThe resulting solids were sequentially washed with nitrobenzene, benzene, and ethanol
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-11f244874f9345b59d3e966aa718e963
Source dataset
uspto-grants-2015_11
Patent number
US09187690B2

Reaction notes

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