Acetic Acid → Benzenamine, 4-chloro-N-ethyl-2-nitro-

HRID 440918

Reaktionsgleichung

Reaktionsgleichung von HRID 440918
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[CH:12](=O)[CH3:13].CC(O)=O.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.N1C=CC=CC=1.CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:12][CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 177Acetaldehyde2×HCID 6422Trifluoroacetic acidHCID 69794-Chloro-2-nitroaniline2×

Produkt 1

HCID 97006Benzenamine, 4-chloro-N-ethyl-2-nitro-Ausbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittel2×HCID 1140TolueneLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

4-chloro-2-nitroaniline (8.6 g; 0.05 mole), acetaldehyde (5.5 ml; 0.05 mole) and HOAc (4.0 ml; 0.1 moles) were dissolved in toluene (100 ml) and stirred for 1 hr. BH3 * pyridine (5.0 ml; 0.01 moles) was added in 1.0 ml increments. The reaction was exothermic, and the reaction progress was monitored by tlc (40%EtOAc/Hexane). Additional TFA, BH3 * pyridine and acetaldehyde were added until the tlc indicated that the 4-chloro-2-nitroaniline was consumed. The reaction mixture was washed 2X with water and placed on a bed of silica and eluted with 20% EtOAc/Hexane. The product was the first major component to elute. The product was crystallized from MeOH which produced 5.0 g (50%) of a yellow crystalline solid.

Aufarbeitung

  1. customwas consumed
  2. washThe reaction mixture was washed 2X with water
  3. washeluted with 20% EtOAc/Hexane
  4. washto elute
  5. customThe product was crystallized from MeOH which

Quellen und Nachweise

ORD-Eintrag
ord-730cd785fd4d49a6a6507551a1e20aeb
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521193

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