Nitric Acid → HCID 86721358, Verbindung

HRID 869528

Reaktionsgleichung

[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5].C(OC(=O)CCC)(=O)CCC.[N+:28]([O-])([OH:30])=[O:29].[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:16]([N+:28]([O-:30])=[O:29])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

[step 1] Methyl 2-(2-methoxyacetamido)benzoate (U.S. Pat. No. 5,091,403; 3.0 g, 13.4 mmol) was suspended in butyric anhydride (12.7 mL, 134.0 mmol), fuming nitric acid (2.3 mL, 51.1 mmol) was added dropwise under ice-cooling, and the mixture was stirred at 0° C. for 40 min. Water was added to the mixture, 4 mol/L aqueous sodium hydroxide solution was added dropwise to neutralize the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-60/40 v/v) to give methyl 2-(2-methoxyacetamido)-3-nitrobenzoate (1.9 g, 51%).

Aufarbeitung

temperaturecooling
additionwas added dropwise
extractionthe mixture was extracted 3 times with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-60/40 v/v)

Quellen und Nachweise

ORD-Eintrag: ord-9cd116c4c1274faea0b7e4769178f31d
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08969345B2

Verknüpfte Notizen

Wird geladen…