Acetic Acid → Methyl 2-(4-amino-3-chlorophenyl)acetate

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Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(O[Na])(C)=O.O.O.O.CC(O)=O>CO.O>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:3][C:2]=1[Cl:1]

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

A mixture of methyl 3-chloro-4-nitrophenylacetate (10.9 g, 47.5 mmol), reduced iron powder (8.58 g, 153.6 mmol), AcONa.3H2O (6.05 g, 44.5 mmol) and AcOH (17.6 ml) in MeOH/H2O (100/400 ml) was heated at 110° C. for 1 h. After cooled to room temperature, the reaction mixture was filtered through Celite and the filtered cake was washed with MeOH. The combined filtrate were evaporated and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on silica gel [150 g, CHCl3/EtOAc (10/1)] to give methyl 4-amino-3-chlorophenylacetate (4.58 g, 48%) as a red oil. 1H-NMR (CDCl3) δ 3.49 (s, 2H), 3.68 (s, 3H), 4.01 (br, 2H), 6.70 (d, J=7.4 Hz, 1H), 6.96 (dd, J=8.1, 2.0 Hz, 1H), 7.17 (d, J=2.0 Hz, 1H).

Aufarbeitung

temperatureAfter cooled to room temperature
filtrationthe reaction mixture was filtered through Celite
washthe filtered cake was washed with MeOH
customThe combined filtrate were evaporated
extractionextracted with EtOAc
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel [150 g, CHCl3/EtOAc (10/1)]

Quellen und Nachweise

ORD-Eintrag: ord-7896521b14b24dcb98f5407f5e44ce06
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07179819B2

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