(3,4-Dimethoxyphenyl)(3-nitrophenyl)methanone → (3-Aminophenyl)(3,4-dimethoxyphenyl)methanone

HRID 1385450노트

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HRID 1385450 반응식
[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]

참가 물질

5

반응물 2

HCID 10803185(3,4-Dimethoxyphenyl)(3-nitrophenyl)methanoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 10563087(3-Aminophenyl)(3,4-dimethoxyphenyl)methanone수율 38.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto afford the crude product
  4. customThe crude product was purified by flash column chromatography (silica gel, 10% ethyl acetate/methylene chloride)

출처 및 근거

ORD 기록
ord-116493795fdc4f948cc267d3a0bb1f4c
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06262101B1

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