Hydrochloric Acid → 2-(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine

HRID 1950051Notes

Reaction equation

HRID 1950051 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N+:19]([O-])=O)[CH2:9][CH2:10]2)=[CH:5][CH:4]=1.Cl>O1CCCC1.CO.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[CH2:7][CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])[CH2:9][CH2:10]2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 230871487-Methoxy-3-(2-nitrophenyl)-1,2-dihydronaphthalene

Product 1

HCID 230875022-(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineYield 70.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-methoxy-3-(2-nitrophenyl)-1,2-dihydronaphthalene (1.5 g) in tetrahydrofuran (10 ml) and methanol (10 ml) were sequentially added 10% palladium-activated charcoal (300 mg) and concentrated hydrochloric acid (0.8 ml), and the solution was stirred for 25 hours at room temperature under a hydrogen atmosphere at 4 atmospheric pressures. After filtration through celite pad, the solution was neutralized with ammonia solution, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo, the resulting solid was washed with a hexane-diethyl ether system to provide the title compound (949 mg).

Workup

  1. filtrationAfter filtration through celite pad
  2. extractionextracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. washthe resulting solid was washed with a hexane-diethyl ether system

Sources & evidence

ORD record
ord-8496773da0e64b149f8af9e0cd63ff0d
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

Loading…