Ethyl-12-(m-nitrophenyl)-11-dodecenoate → Ethyl-12-(m-aminophenyl)-dodecanoate

HRID 2226288노트

반응식

HRID 2226288 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1)[CH3:2]

참가 물질

4

반응물 1

HCID 53714556Ethyl-12-(m-nitrophenyl)-11-dodecenoate

생성물 1

HCID 14584161Ethyl-12-(m-aminophenyl)-dodecanoate수율 97.5%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

Ethyl-12-(m-nitrophenyl)-11-dodecenoate (9.76 g, 28.1 mmol was dissolved in ethyl acetate (55 ml). The solution was hydrogenated over 5% Pd/C (0.346 g) at room temperature and at an initial pressure of 45 psi for four hours. The reaction mixture was filtered through Celite and the solvent was removed under reduced pressure to yield an oily residue. The crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1) to yield the reduced compound 5, ethyl-12-(m-aminophenyl)-dodecanoate (8.75 g, 97.5% yield).

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed under reduced pressure
  3. customto yield an oily residue
  4. customThe crude product was purified by column chromatography (80 g silica gel, hexanes:ethyl acetate, discontinuous gradient 10:1-2:1)

출처 및 근거

ORD 기록
ord-fe1c7b133eb34c13ba00377209685fea
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05347030

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