Nitric Acid → Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

HRID 871960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871960
S(=O)(=O)(O)O.[C:6]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([Br:20])=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16])(=[O:8])[CH3:7].[N+:21]([O-])([OH:23])=[O:22]>O>[C:6]([NH:9][C:10]1[C:19]([N+:21]([O-:23])=[O:22])=[C:14]([C:13]([Br:20])=[CH:12][CH:11]=1)[C:15]([O:17][CH3:18])=[O:16])(=[O:8])[CH3:7]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 58891822Methyl 5-acetamido-2-bromobenzoate

Produkt 1

HCID 11151255Methyl 3-acetylamino-6-bromo-2-nitrobenzoateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To conc. sulfuric acid (150 mL), methyl 5-acetylamino-2-bromobenzoate (Reference Compound No. 1-(2), 18.5 g, 68.1 mmol) was added at 0° C. portionwise, and conc. nitric acid (150 mL) was added dropwise thereto over 1 hour. The reaction mixture was stirred for 30 minutes, poured into iced water (1 L), and then extracted with ethyl acetate (500 mL, 2 times). The organic layer was washed with water (1 L, 2 times), saturated aqueous sodium hydrogen carbonate solution (1 L), and saturated brine (1 L) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (13.4 g) as a yellow solid. (Yield 62%)

Aufarbeitung

  1. addition1-(2), 18.5 g, 68.1 mmol) was added at 0° C. portionwise
  2. extractionextracted with ethyl acetate (500 mL, 2 times)
  3. washThe organic layer was washed with water (1 L, 2 times), saturated aqueous sodium hydrogen carbonate solution (1 L), and saturated brine (1 L) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3e456e6a894c4d10a6f719a62fd6f293
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08975256B2

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