3-Methyl-6-(methyloxy)-1-[(4-nitrophenyl)oxy]-2-phenylnaphthalene → 4-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}aniline

HRID 1992840Notes

Reaction equation

HRID 1992840 reaction equation
[CH3:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2>CCO.O=[Pt]=O>[CH3:1][C:2]1[C:3]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2

Participants

4

Reactant 1

HCID 685397753-Methyl-6-(methyloxy)-1-[(4-nitrophenyl)oxy]-2-phenylnaphthalene

Product 1

HCID 685373984-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}anilineYield 100.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

PtO2 (10 mg) was added to a solution of 37 (490 mg, 1.27 mmol, 1 equiv) in EtOH (5 mL). The reaction mixture was stirred under an atmosphere of H2 (50 psi) for 1.5 h. The mixture was then filtered thru a pad of celite and concentration down to provide 38 (452 mg, 100%) as a clear oil. 1HNMR (400 MHz, DMSO-d6): δ 7.61 (m, 2H), 7.32-7.23 (m, 4H), 7.16 (m, 2H), 7.02 (m, 1H), 6.32-6.26 (m, 4H), 5.74 (br s, 2H), 3.85 (s, 3H), 2.14 (s, 3H). MS m/z 356.2 (M+H)+.

Workup

  1. filtrationThe mixture was then filtered thru
  2. concentrationa pad of celite and concentration down

Sources & evidence

ORD record
ord-df00a49bbbb74a2f826db2f629b40628
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…