3-Nitrophenol → N-cyclopropyl-2-(3-nitrophenoxy)acetamide

HRID 1487106

Reaktionsgleichung

[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[CH2:12][C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)=[O:14].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH:16]1([NH:15][C:13](=[O:14])[CH2:12][O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:18][CH2:17]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 3-nitrophenol (4 g, 28.8 mmol), 2-chloro-N-cyclopropylacetamide (4.61 g, 34.5 mmol), K2CO3 (7.95 g, 57.5 mmol) and 18-CROWN-6 (0.228 g, 0.863 mmol) in N,N-Dimethylformamide (30.0 ml) was stirred under N2 atmosphere for 18 hrs at 50° C. After cooling to RT, the reaction mixture was partitioned between EtOAc (250 ml) and water (250 ml). Aq. phase was re-extracted with EtOAc (200 ml). Combined organic layer was washed with brine (100 ml), dried over sodium sulphate and the solvent was evaporated under vacuum. Crude residue was purified by flash chromatography to obtain N-cyclopropyl-2-(3-nitrophenoxy)acetamide (4.21 gm).

Aufarbeitung

temperatureAfter cooling to RT
customthe reaction mixture was partitioned between EtOAc (250 ml) and water (250 ml)
extractionAq. phase was re-extracted with EtOAc (200 ml)
washCombined organic layer was washed with brine (100 ml)
dry with materialdried over sodium sulphate
customthe solvent was evaporated under vacuum
customCrude residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-2cf8359757694e178b0fe0770e9370cb
Quelldatensatz: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09428499B2

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