1-(4-Nitro-phenyl)-cyclopropanecarboxylic acid methyl ester → Methyl 1-(4-aminophenyl)cyclopropane-1-carboxylate

HRID 503280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 503280
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Komponenten

4

Edukt 1

HCID 591294291-(4-Nitro-phenyl)-cyclopropanecarboxylic acid methyl ester

Produkt 1

HCID 58841079Methyl 1-(4-aminophenyl)cyclopropane-1-carboxylateAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of methyl 1-(4-nitrophenyl)cyclopropanecarboxylate (20 g, 0.09 mol) in MeOH (400 mL) was added Ni (2 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off through a pad of Celite and the filtrate was evaporated under vacuum to give crude product, which was purified by chromatography column on silica gel (petroleum ether/ethyl acetate=10:1) to give methyl 1-(4-aminophenyl)cyclopropanecarboxylate (11.38 g, 66%). 1H NMR (300 MHz, CDCl3) δ7.16 (d, J=8.1 Hz, 2H), 6.86 (d, J=7.8 Hz, 2H), 4.31 (br, 2H), 3.61 (s, 3H), 1.55-1.50 (m, 2H), 1.30-1.12 (m, 2H).

Aufarbeitung

  1. filtrationThe catalyst was filtered off through a pad of Celite
  2. customthe filtrate was evaporated under vacuum
  3. customto give crude product, which
  4. customwas purified by chromatography column on silica gel (petroleum ether/ethyl acetate=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-58125a35b63148dc8c408eb4070134e7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776905B2

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