Ammonia → 2-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene

HRID 1950039Notes

Reaction equation

HRID 1950039 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28])CCC.[Cl-].[Li+].N>CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[N+:27]([O-:29])=[O:28])[CH:9]=2)[CH:4]=1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 787862-Bromo-6-methoxynaphthaleneHCID 433294Lithium ChlorideHCID 23087474Tributyl(4-methoxy-2-nitrophenyl)tin

Product 1

HCID 230875562-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthaleneYield 63.2%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was synthesized by referring to J. Am. Chem. Soc., 1999, 121, 760. A suspension of 6-methoxy-2-bromonaphthalene (500 mg), tributyl(4-methoxy-2-nitrophenyl)tin (1.1 g), tetrakis(triphenylphosphine)palladium(0) (250 mg), copper(I) chloride (1.0 g) and lithium chloride (540 mg) in dimethylsulfoxide (15 ml) was stirred at 60° C. for 5 hours under a nitrogen atmosphere. Ethyl acetate and aqueous ammonia were sequentially added thereto, the solution was filtered through celite pad, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was washed with a hexane-diethyl ether system to provide the title compound (412 mg).

Workup

  1. customThe title compound was synthesized
  2. filtrationthe solution was filtered through celite pad
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. washThe residue was washed with a hexane-diethyl ether system

Sources & evidence

ORD record
ord-54e0a600cc4941f8a3d85b5e479c0410
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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