(3,4-Dimethoxyphenyl)(3-nitrophenyl)methanone → (3-Aminophenyl)(3,4-dimethoxyphenyl)methanone
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:7].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)=[O:7]Participants
Procedure
To a solution of 3,4-dimethoxy-3′-nitrobenzophenone (0.5 g, 1.7 mmol) in 40 mL of ethyl acetate was added 0.05 g of 10% palladium on carbon catalyst. The mixture was hydrogenated in a Parr-Shaker apparatus at 55-60 psi of hydrogen for 1.5 hours. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to afford the crude product. The crude product was purified by flash column chromatography (silica gel, 10% ethyl acetate/methylene chloride) to afford 0.17 g (38%) of the product as a yellow solid: mp 157-175° C.; 1H NMR (CDCl3) δ7.56-6.80 (m, 7 H); 3.95 (s, 3 H), 3.94 (s, 3 H); 13C NMR (CDCl3) δ195.7, 152.9, 148.9, 146.4, 139.3, 130.3, 128.9, 125.4, 120.1, 118.4, 115.6, 112.1, 109.7, 56.0, 56.0; Anal. Calcd for C15H15NO3. Theoretical: C, 70.02; H, 5.88; N, 5.44. Found: C, 70.00; H, 6.10; N, 5.13.
Workup
- filtrationThe reaction mixture was filtered through celite
- concentrationthe filtrate was concentrated in vacuo
- customto afford the crude product
- customThe crude product was purified by flash column chromatography (silica gel, 10% ethyl acetate/methylene chloride)
Sources & evidence
- ORD record
- ord-116493795fdc4f948cc267d3a0bb1f4c
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06262101B1
Reaction notes
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