Acetic Acid → 1-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline

HRID 1531974Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1531974
S(=O)(=O)(O)[OH:2].[N+:6]([O-:9])(O)=[O:7].[C:10]([N:13]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([Br:23])=[C:19]([CH3:22])[CH:20]=2)[CH:15]([CH2:25][C:26](=[C:30]=[O:31])OCC)[CH2:14]1)(=[O:12])[CH3:11].[CH3:32][C:33](O)=O>>[C:10]([N:13]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([Br:23])=[C:19]([CH3:22])[C:20]=2[N+:6]([O-:9])=[O:7])[CH:15]([CH2:25][CH2:26][C:30]([O:31][CH2:32][CH3:33])=[O:2])[CH2:14]1)(=[O:12])[CH3:11]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 867565351-Acetyl-5-bromo-3-(2-ethoxy-carbonylethyl)-4,6-dimethylindoline

Produkt 1

HCID 222473011-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline

Versuchsvorschrift

To a mixture of AcOH (10 ml), conc. sulfuric acid (10 ml) and nitric acid (0.55 ml) was added by portions 1-acetyl-5-bromo-3-(2-ethoxy-carbonylethyl)-4,6-dimethylindoline (3.0 g) at 0° C., and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was poured into ice water and extracted with CHCl3 (100 ml). After washing with water, the mixture was dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=50/1−10/1) to give 2.7 g of 1-acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline.

Aufarbeitung

  1. extractionextracted with CHCl3 (100 ml)
  2. washAfter washing with water
  3. dry with materialthe mixture was dried over anhydrous sodium sulfate
  4. customCHCl3 was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: CHCl3/MeOH=50/1−10/1)

Quellen und Nachweise

ORD-Eintrag
ord-2b96d873fb67480bb4f40c60b4cb51f5
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06200988B1

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