Nitric Acid → 4-Bromo-7-nitro-2,3-dihydro-isoindol-1-one

HRID 1247447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247447
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:11]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 219075094-Bromoisoindolin-1-one

Produkt 1

HCID 219075574-Bromo-7-nitro-2,3-dihydro-isoindol-1-oneAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 0° C. solution of Example 1C (5 g, 23.6 mmol) in 10 mL sulfuric acid was treated with a solution of concentrated nitric acid (1.55 mL, 24.7 mmol) in 10 mL sulfuric acid via addition funnel. The resulting mixture was stirred at 0° C. for 1 hour, warmed to room temperature, stirred overnight, poured over ice, and filtered. The filter cake was washed with water and diethyl ether and then dried to give 5.39 g of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 4.39 (s, 2H); 7.88 (d, J=8.1 Hz, 1H); 8.05 (d, J=8.5 Hz, 1H); 9.17 (s, 1H).

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. additionpoured over ice
  4. filtrationfiltered
  5. washThe filter cake was washed with water and diethyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a487b3064f77409c929c07e10e806b0b
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129260B2

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