6-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene → 6-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthalene
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:11]=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=[CH:13]4)[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:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([O:20][CH3:21])[CH:14]=[CH:13]2Participants
Procedure
6-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene 45 (260 mg, 0.81 mmol) was hydrogenated overnight in ethyl acetate (35 mL) at 40˜45 lb./sq. in. using 10% palladium on carbon (70 mg) as catalyst. The reaction solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration of the ethyl acetate solution in vacuo gave the crude product. The residue was chromatographed using a 75:25 mixture of hexanes:ethyl acetate to give 46 (180 mg) in 76% yield; mp 130-132° C.; IR (KBr) 3463, 3372, 2874, 1631, 1494, 1441, 1389, 1260, 1187cm−1; UV (MeOH) 234 nm (log ε=4.73); 1H NMR (CDCl3) δ3.56 (2H, s), 3.95 (3H, s), 5.92 (2H, s), 6.40 (1H, s), 6.75 (1H, s), 7.17-7.22 (2H, m), 7.51 (1H, dd, J1=8.5, J2=1.6), 7.73-7.82 (3H, m); 13C NMR δ55.84, 98.33, 101.25, 106.11, 110.71, 119.66, 120.30, 127.79, 128.27, 128.61, 129.60, 129.91, 133.95, 135.11, 138.95, 141.17, 148.05, 158.29; HRMS (EI) calcd for C18H15NO3 m/z: 293.1052; found: 293.1051.
Workup
- washthe catalyst was washed with ethyl acetate (10 mL×3)
- customConcentration of the ethyl acetate solution in vacuo gave the crude product
- customThe residue was chromatographed
- additiona 75:25 mixture of hexanes
Sources & evidence
- ORD record
- ord-a44cff7916a04de489a58bf51886027c
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06740650B2
Reaction notes
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