1,10-Phenanthroline → 4-Methyl-N-(4-methylphenyl)-N-phenylbenzenamine

HRID 871820Notes

Reaction equation

HRID 871820 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[K+].N1[C:31]2[C:22](=[CH:23][CH:24]=[C:25]3[C:30]=2N=CC=C3)C=CC=1.IC1C=CC=CC=1>Cl[Cu].C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C:22]2[CH:31]=[CH:30][CH:25]=[CH:24][CH:23]=2)[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11575IodobenzeneHCID 14797Potassium HydroxideHCID 69293Benzenamine, 4-methyl-N-(4-methylphenyl)-

Product 1

HCID 885394-Methyl-N-(4-methylphenyl)-N-phenylbenzenamine

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

4,4′-dimethyldiphenylamine (0.99 g, 5.0 mmol), KOH (2.52 g, 45.0 mmol), CuCl (99 mg, 1.0 mmol) and 1,10-phenanthroline (180 mg, 1.0 mmol) were charged in a two-necked bottle. The bottle was deoxygenated and purged with nitrogen, and added dried toluene (12 mL) and iodobenzene (0.67 ml, 6.0 mmol). The reaction was heated to 120° C., and stirred for 12 hours. The resulting was filtered to remove metal and then concentrated under reduced pressure and the residue was purified by column chromatography (hexanes/CH2Cl2=1/1) to afford G (916 g, 67%) as white solid.

Workup

  1. customThe bottle was deoxygenated
  2. custompurged with nitrogen
  3. filtrationThe resulting was filtered
  4. customto remove metal
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (hexanes/CH2Cl2=1/1)
  7. customto afford G (916 g, 67%) as white solid

Sources & evidence

ORD record
ord-a293430a55ae4ea687c77bdef8febb2a
Source dataset
uspto-grants-2015_03
Patent number
US08974920B2

Reaction notes

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