6-(4,5-Dimethoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene → 2-(6,7-Dimethoxynaphthalen-2-yl)-4,5-dimethoxyaniline

HRID 1582876Notes

Reaction equation

HRID 1582876 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([O:21][CH3:22])[C:15]([O:23][CH3:24])=[CH:14]3)=[C:5]([N+:25]([O-])=O)[CH:4]=1>C(OCC)(=O)C.[Pd]>[NH2:25][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[CH:7][C:6]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([O:21][CH3:22])[C:15]([O:23][CH3:24])=[CH:14]2

Participants

4

Reactant 1

HCID 227164246-(4,5-Dimethoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene

Product 1

HCID 227164342-(6,7-Dimethoxynaphthalen-2-yl)-4,5-dimethoxyanilineYield 108%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

6-(4,5-Dimethoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene (12 mg, 0.03 mmol) was hydrogenated overnight in ethyl acetate (20 mL) at 40-45 lb./sq. in. under catalysis of palladium (10 wt % on activated carbon, 10 mg). The solution was passed through celite bed and the catalyst was washed with ethyl acetate (3×10 mL). Concentration in vacuo gave the crude product. Chromatography using 65:35 hexanes:ethyl acetate gave compound 18 (11 mg) in nearly 100% yield; 1H NMR (CDCl3) d 3.84(3H, s), 3.89(3H, s), 4.01(3H, s), 4.02(3H, s), 6.41(1H, s), 6.80(1H, s), 7.14(1H, s), 7.15(1H, s), 7.43(1H, dd, J=8.4, J=1.6), 7.75(1H, d, J=1.5), 7.75(1H, d, J=8.4); 13C NMR d 56.4, 57.2, 101.3, 106.6, 106.8, 115.2, 119.9, 126.2, 126.8, 127.3, 128.5, 129.9, 135.7, 138.0, 142.7, 149.8, 150.1, 150.3.

Workup

  1. washthe catalyst was washed with ethyl acetate (3×10 mL)
  2. concentrationConcentration in vacuo
  3. customgave the crude product

Sources & evidence

ORD record
ord-eb9e517f7d454fe6abb0e5ff65a6f87f
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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