7-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene → 7-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthalene

HRID 1582894Notes

Reaction equation

HRID 1582894 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([C:10]3[CH:19]=[C:18]4[C:13]([CH:14]=[CH:15][C:16]([O:20][CH3:21])=[CH:17]4)=[CH:12][CH:11]=3)[CH:7]=2)[O:2]1>C(OCC)(=O)C.[Pd]>[NH2:22][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:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([O:20][CH3:21])=[CH:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 227164227-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene

Product 1

HCID 227164427-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthaleneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene 48 (100 mg, 0.31 mmol) was hydrogenated overnight in ethyl acetate (35 mL) at 40˜45 lb./sq. in. using 10% palladium on carbon (30 mg) as catalyst. The reaction solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). The ethyl acetate solution was concentrated in vacuo gave the crude product. The residue was chromatographed using a 75:25 mixture of hexanes:ethyl acetate to give 49 (75 mg) in 83% yield; IR (KBr) 3426, 3366, 2364, 2339, 1629, 1503, 1487, 1467, 1233, 1215, 1187 cm−1; 1H NMR (CDCl3) δ3.64 (2H, s), 3.94 (3H, s), 5.92 (2H, s), 6.40 (1H, s), 6.76 (1H, s), 7.15-7.20 (2H, m), 7.40 (1H, dd, J1=8.3, J2=1.7), 7.75-7.85 (3H, m); 13C NMR δ55.83, 98.35, 101.27, 106.25, 110.65, 119.35, 120.29, 125.82, 127.35, 128.31, 128.72, 129.67, 135.34, 137.99, 138.99, 141.17, 148.16, 158.49; HRMS (EI) calcd for C18H15NO3 m/z: 293.1052; found: 293.1052.

Workup

  1. washthe catalyst was washed with ethyl acetate (10 mL×3)
  2. concentrationThe ethyl acetate solution was concentrated in vacuo
  3. customgave the crude product
  4. customThe residue was chromatographed
  5. additiona 75:25 mixture of hexanes

Sources & evidence

ORD record
ord-c94c00c0049e48c8bd494bae52437c46
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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