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

HRID 1017933노트

반응식

HRID 1017933 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) δ 7.56-6.80 (m, 7 H); 3.95 (s, 3 H), 3.94 (s, 3 H); 13C NMR (CDCl3) δ 195.7, 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-084f6e4e42ee44f0961242ca52ccecc6
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479554B2

반응 노트

불러오는 중…