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

HRID 1884036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1884036
[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

Komponenten

4

Edukt 1

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

Produkt 1

HCID 232338ethyl 4-(4-aminophenyl)-4-oxobutanoateAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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=6.5 Hz, 2H, CH2), 4.04 (q, J=7 Hz, 2H, esterCH2), 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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-e38833aff2c741f4b85f0e217210bd29
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762188B1

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