Nitric Acid → N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1485

Reaktionsgleichung

Reaktionsgleichung von HRID 1485
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:12]3[CH2:13][CH2:14][CH2:15][CH2:16][C:11]=3[C:9]2=[O:10])=[C:4]([F:19])[CH:3]=1.[N+:20]([O-])([OH:22])=[O:21]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:20]([O-:22])=[O:21])=[CH:6][C:5]([N:8]2[C:9](=[O:10])[C:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:17]2=[O:18])=[C:4]([F:19])[CH:3]=1

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 1859312-(4-Chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-1h-isoindole-1,3(2h)-dione

Produkt 1

HCID 15590179N-(4-chloro-2-fluoro-5-nitrophenyl)-3,4,5,6-tetrahydrophthalimideAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-3 °C

Versuchsvorschrift

A mixture of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide (24.4 g, 86.7 mmol) in sulfuric acid (150 mL) is cooled to -3° C., treated dropwise with nitric acid (70% real, 6.70 mL, 104 mmol) while maintaining the temperature at 0°-2° C., stirred at room temperature for 90 minutes, and poured onto ice. The aqueous mixture is stirred for several minutes, and filtered to obtain a solid which is washed with water and dried to give the title product as a white powder (28.6 g, mp 152°-155° C.).

Aufarbeitung

  1. temperaturewhile maintaining the temperature at 0°-2° C.
  2. additionpoured onto ice
  3. stirringThe aqueous mixture is stirred for several minutes
  4. filtrationfiltered
  5. customto obtain a solid which
  6. washis washed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1b12023f2a354fce9ed4c6252aa46b2d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726126

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