2-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene → 5-Methoxy-2-(6-methoxynaphthalen-2-yl)phenylamine

HRID 1950040Notes

Reaction equation

HRID 1950040 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[N+:21]([O-])=O)[CH:9]=2)[CH:4]=1>O1CCCC1.CO.[Pd]>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]=2)=[C:14]([NH2:21])[CH:15]=1

Participants

5

Reactant 1

HCID 230875562-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene

Product 1

HCID 230875115-Methoxy-2-(6-methoxynaphthalen-2-yl)phenylamineYield 80.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene (390 mg) in tetrahydrofuran (6 ml) and methanol (6 ml) was added 10% palladium-activated charcoal (100 mg), and the solution was stirred overnight at room temperature under a hydrogen atmosphere at ambient pressure. After filtration through celite pad, the solvent was evaporated in vacuo, and the resulting solid was washed with a hexane-diethyl ether system to provide the title compound (285 mg).

Workup

  1. filtrationAfter filtration through celite pad
  2. customthe solvent was evaporated in vacuo
  3. washthe resulting solid was washed with a hexane-diethyl ether system

Sources & evidence

ORD record
ord-73a6f92f13794b688269bd8f9b7613ed
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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