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

HRID 381592노트

반응식

HRID 381592 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 (100 g) eluting with ethyl acetate:hexane (1:2) to give ethyl 4-(4-aminophenyl)-4-oxobutyrate (0.38 g) as a white solid. 1H NMR (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=z 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 (100 g)
  5. washeluting with ethyl acetate:hexane (1:2)

출처 및 근거

ORD 기록
ord-c715a678d2104e1185e5678f274b1e79
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306865B1

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