6-Methoxy-2-(4-methoxy-2-nitrophenyl)-1,1-dimethyl-1,4-dihydronaphthalene → 5-Methoxy-2-(6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine

HRID 1950083Notes

Reaction equation

HRID 1950083 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[C:8]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[N+:23]([O-])=O)=[CH:7][CH2:6]2>O1CCCC1.CO.[Pd]>[CH3:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]2([CH3:14])[CH3:13])=[C:16]([NH2:23])[CH:17]=1

Participants

5

Reactant 1

HCID 230875336-Methoxy-2-(4-methoxy-2-nitrophenyl)-1,1-dimethyl-1,4-dihydronaphthalene

Product 1

HCID 230871285-Methoxy-2-(6-methoxy-1,1-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-methoxy-2-(4-methoxy-2-nitrophenyl)-1,1-dimethyl-1,4-dihydronaphthalene (433 mg) in tetrahydrofuran (6 ml) and methanol (6 ml) was added 10% palladium-activated charcoal (200 mg), and the solution was stirred for 3.5 hours at room temperature under a hydrogen atmosphere at 4 atmospheric pressures. After filtration through celite pad, the solvent was evaporated in vacuo, and the resulting solid was washed with hexane-diethyl ether system to provide the title compound (314 mg).

Workup

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

Sources & evidence

ORD record
ord-c4d1a10581e444a69d905539fb027b67
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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