HCID 54039567, 화합물 → 3-(3,4-Dimethoxyphenyl)-3-(3-aminophenyl)acrylonitrile

HRID 583451

반응식

HRID 583451 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)=[CH:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:21][C:17]1[CH:16]=[C:15]([C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][C:13]#[N:14])[CH:20]=[CH:19][CH:18]=1

참가 물질

5

반응물 2

HCID 54039567HCID 54039567, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 537858693-(3,4-Dimethoxyphenyl)-3-(3-aminophenyl)acrylonitrile수율 56%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-(3,4-dimethoxyphenyl)-3-(3'-nitrophenyl)acrylonitrile (0.7 g, 2.3 mmol) in 40 mL of ethyl acetate was added 0.1 g of 10% palladium on carbon catalyst. The mixture was hydrogenated in a Parr-Shaker apparatus at 55-60 psi of hydrogen for 2.5 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, 15% ethyl acetate/methylene chloride) to afford 0.25 g (56%) of a mixture of the E and Z isomers as a yellow solid: mp 100-101° C.; 1H NMR (CDCl3) δ 7.30-6.59 (m, 14H); 5.63 (s, 1H), 5.59 (s, 1H), 3.94 (s, 3H), 3.87 (s, 3H), 3.84 (s, 3H); 13C NMR (CDCl3) δ 163.1, 162.9, 151.1, 150.5, 148.8, 148.7, 146.5, 146.4, 140.4, 138.2, 131.5, 129.5, 129.5, 129.4, 123.2, 122.1, 119.9, 119.0, 118.4, 118.2, 116.8, 116.6, 115.9, 115.0, 112.7, 111.0, 110.7, 93.3, 92.7, 56.1, 56.0, 55.9; Anal. Calcd for C17H16N2O3. Theoretical: C, 72.84; H, 5.75; N, 9.99. Found: C, 72.48; H, 6.05; N, 9.58.

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, 15% ethyl acetate/methylene chloride)

출처 및 근거

ORD 기록
ord-275f72674201451da034d0e4f6cef422
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929117

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