N-phenyl-2-naphthylamine → HCID 57232163, compound

HRID 1903584Notes

Reaction equation

HRID 1903584 reaction equation
[C:1]1([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:19]1[CH:20]=[C:21]([O:25][CH3:26])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].[N+](C1C=CC=CC=1)([O-])=O>[C:1]1([N:7]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8679N-phenyl-2-naphthylamineHCID 11430Potassium CarbonateHCID 69839Benzene, 1-iodo-3-methoxy-

Product 1

HCID 57232163HCID 57232163, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7416NitrobenzeneSolvent

Procedure

A mixture of 43.8 g (0.2 mol) of phenyl-β-naphthylamine, 46.8 g (0.2 mol) of m-iodoanisol, 27.6 g (0.2 mol) of anhydrous potassium carbonate, 2 g of copper powder and 300 ml of nitrobenzene was heated under reflux for 15 hours. The inorganic substances were filtered off and the nitrobenzene was distilled off. The residue obtained was then processed by column chromatography to obtain 43.8 g of phenyl-β-naphthyl-3-methoxyphenylamine.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours
  3. filtrationThe inorganic substances were filtered off
  4. distillationthe nitrobenzene was distilled off
  5. customThe residue obtained

Sources & evidence

ORD record
ord-ddd48cbc0be34e20a7fdbda30a4f517c
Source dataset
uspto-grants-1984_03
Patent number
US04436920

Reaction notes

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