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

HRID 2166907Notes

Reaction equation

HRID 2166907 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-9d6d89df14a044fd91424c321d03022e
Source dataset
uspto-grants-1983_06
Patent number
US04390616

Reaction notes

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