6-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxynaphthalene → 6-(2-Amino-4,5-methylenedioxyphenyl)-2,3-dimethoxy-naphthalene

HRID 1582873Notes

Reaction equation

HRID 1582873 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([N+:24]([O-])=O)=[C:6]([C:10]3[CH:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([O:20][CH3:21])[C:14]([O:22][CH3:23])=[CH:13]4)[CH:7]=2)[O:2]1>C(OCC)(=O)C.[Pd]>[NH2:24][C:5]1[CH:4]=[C:3]2[O:2][CH2:1][O:9][C:8]2=[CH:7][C:6]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([O:20][CH3:21])[C:14]([O:22][CH3:23])=[CH:13]2

Participants

4

Reactant 1

HCID 227164206-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxynaphthalene

Product 1

HCID 227164376-(2-Amino-4,5-methylenedioxyphenyl)-2,3-dimethoxy-naphthaleneYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

6-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxynaphthalene (25 mg, 0.071 mmol) was hydrogenated overnight in ethyl acetate (40 mL) at 40˜45 lb./sq. in. under catalysis of palladium (10 wt % on activated carbon, 20 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 60:40 hexanes:ethyl acetate gave compound 13 (15 mg) in 66% yield; 1H NMR (CDCl3) d 4.01(3H, s), 4.02(3H, s), 5.91(2H, s), 6.40(1H, s), 6.73(1H, s), 7.13(1H, s), 7.15(1H, s), 7.39(1H, dd, J=8.2, J=1.8), 7.72(1H, s), 7.74(1H, d, J=8.5); 13C NMR d 56.4, 98.3, 101.2, 106.6, 106.8, 110.7, 120.5, 126.3, 127.0, 127.3, 128.5, 129.9, 135.7, 138.9, 141.1, 148.0, 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-6bf87feb322e406fada57e7b711db28b
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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