Methyl 4-(4-nitrophenyl)butanoate → Methyl 4-aminobenzenebutanoate

HRID 885701

Reaktionsgleichung

Reaktionsgleichung von HRID 885701
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=1)([O-])=O.[N+](C1C=CC=CC=1CCCC(OC)=O)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 140721Methyl 4-(4-nitrophenyl)butanoateHCID 11401810Methyl 4-(2-nitrophenyl)butanoate

Produkt 1

HCID 88628Methyl 4-aminobenzenebutanoateAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of methyl 4-(4-nitrophenyl)butanoate and methyl 4-(2-nitrophenyl)butanoate (2.24 g, 10.03 mmol) and 0.2 g of 10% Pd/C in 40 mL of methanol was vigorously stirred under hydrogen air. The mixture was stirred for 4 h at room temperature (monitored by TLC), and filtered through Celite. The solvent was evaporated. The residue was purified by chromatography to give the title compound (0.80 g, 41%): NMR (400 MHz in CDCl3, Bruker AVANCE-400): δ 1.89 (m, 2H, CH2), 2.31 (t, 2H, CH2—CH2—COOMe), 2.53 (t, 2H, CH2), 3.58 (br, 2H, NH2), 3.65 (s, 3H, OMe), 6.61 (d, 2H, J=3.5 Hz, Ar—H), 6.95 (d, 2H, J=3.4 Hz).

Aufarbeitung

  1. stirringThe mixture was stirred for 4 h at room temperature (monitored by TLC)
  2. filtrationfiltered through Celite
  3. customThe solvent was evaporated
  4. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-df227695f252421484b0bc9c38fb9c17
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242282B2

Verknüpfte Notizen

Wird geladen…