1-Methylimidazole → Butyl 3-(3-(methylamino)-4-nitrophenyl)prop-2-enoate
Reaktionsgleichung
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][CH3:12])[CH:3]=1.[Li+].[Cl-].CCN(C(C)C)C(C)C.[C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])(=[O:27])[CH:25]=[CH2:26].CN1C=CN=C1>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:12][NH:11][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[CH:26]=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:27]Komponenten
8
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
To a mixture of 4-chloro-2-methylaminonitrobenzene (50.0 g, 268.0 mmol, 1.0 eq), Pd(OAc)2 (0.30 g, 1.3 mmol, 0.005 eq) and LiCl (11.4 g 268.0 mmol, 1.0 eq) in DMAc (250 mL) was added iPr2NEt (56 mL, 321.5 mmol, 1.2 eq) followed by n-butyl acrylate (40 mL, 281.4 mmol, 1.05 eq) under nitrogen. The reaction mixture was stirred at 110° C. for 12 h, then cooled to 50° C. 1-methylimidazole (10.6 mL, 134.0 mmol, 0.5 eq) was added and the mixture was stirred for 30 min before filtering and adding water (250 mL). The resulting mixture was cooled to r.t. over 1 h. The resulting solid was filtered and washed with water and dried to yield n-butyl 3-methylamino-4-nitrocinnamate (71.8 g, 96%, 99.2 A % purity).
Aufarbeitung
- temperaturecooled to 50° C
- stirringthe mixture was stirred for 30 min
- filtrationbefore filtering
- additionadding water (250 mL)
- temperatureThe resulting mixture was cooled to r.t. over 1 h
- filtrationThe resulting solid was filtered
- washwashed with water
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-d425e3b5424740d19c088e94c7ec6394
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08598183B2
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