Ethyl 4-(4-nitrophenyl)-4-oxobutanoate → ethyl 4-(4-aminophenyl)-4-oxobutanoate

HRID 2289270노트

반응식

HRID 2289270 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1

참가 물질

4

반응물 1

HCID 15535281Ethyl 4-(4-nitrophenyl)-4-oxobutanoate

생성물 1

HCID 232338ethyl 4-(4-aminophenyl)-4-oxobutanoate수율 30.7%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of ethyl 4-(4-nitrophenyl)-4-oxobutyrate (1.4 g, 5.6 mmol) and 10% palladium on carbon (0.18 g) in ethanol (50 ml) was shaken under hydrogen (50 psi) for 2 hours then filtered and concentrated in vacuo. The residue was absorbed onto silica gel (5 g) from an ethyl acetate solution and purified by chromatography on silica gel (10 g) eluting with ethyl acetate:hexane (1:2) to give ethyl 4 -(4-aminophenyl)-4-oxobutyrate (0.38 g) as a white solid. 4NMR (DMSO-d6, 300 MHz) δ: 1.17 (t, J=7 Hz, 3H, CH3), 2.56 (t, J=6.5 Hz, 2H, CH2), 3.10 (t, J=6.5 Hz, 2H, CH2), 4.04 (q, J=7 Hz, 2H, ester CH2), 6.04 (br s, 2H, NH2), 6.57 (d, J=9 Hz, 2H, Ar), 7.69 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C12H15NO3 : C, 65.14; H, 6.83; N, 6.33. Found: C, 65.23; H, 6.85; N, 6.32.

후처리

  1. filtrationthen filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed onto silica gel (5 g) from an ethyl acetate solution
  4. custompurified by chromatography on silica gel (10 g)
  5. washeluting with ethyl acetate:hexane (1:2)

출처 및 근거

ORD 기록
ord-2c23d9bc605a4acf9bce034703d7df82
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090941

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