Sulfuric Acid → 3-Chloro-5-ethylnitrobenzene

HRID 326639

Reaktionsgleichung

Reaktionsgleichung von HRID 326639
[Cl:1][C:2]1[C:7](N)=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([CH2:12][CH3:13])[CH:3]=1.OS(O)(=O)=O>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[C:4]([CH2:12][CH3:13])[CH:3]=1

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 197351662-Chloro-4-ethyl-6-nitroaniline

Produkt 1

HCID 197352173-Chloro-5-ethylnitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 6-chloro-4-ethyl-2-nitroaniline (5.3 g) in ethanol (40 ml) was added c.H2SO4 (5 ml) dropwise. The solution was heated to reflux and solid NANO2 (4.55 g) was added in small portions over 25 minutes. After a further 1 h at reflux the mixture was poured onto ice and extracted with ethyl acetate. The organic phase was washed with water (×3) and brine (×3), dried over MGSO4 and evaporated. 3-Chloro-5-ethylnitrobenzene was isolated as a yellow oil (4.0 g) after silica chromatography. δ (60 MHz, CDCl3) 1.2 (3H, t, CH3), 2.5 (2H, q, CH2), 7.5 (1H, s, Ar) and 7.9 (2H, s, Ar). This product was treated with iron powder (2.7 g) in acetic acid (40 ml) and ethanol (30 ml) at reflux for 2.5 h. The mixture was filtered through celite and the solvent evaporated. The residual oil was diluted with hexane (2 ml) and chromatographed on silica, eluting with 20% CHCl3 /hexane. 3-Chloro-5-ethylaniline (0.9 g) was isolated as a pure oil. δ (360 MHz, CDCl3) 1.19 (3H, t, CH3), 2.52 (2H, q, CH2), 3.20 (2H, s, NH2), 6.38 (1H, dd, Ar), 6.49 (1H, dd, Ar) and 6.58 (1H, dd, Ar).

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. additionsolid NANO2 (4.55 g) was added in small portions over 25 minutes
  4. temperatureAfter a further 1 h at reflux the mixture
  5. additionwas poured onto ice
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with water (×3) and brine (×3)
  8. customdried over MGSO4
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0fe94976548c40f0a9b7b208c3adf67c
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270309

Verknüpfte Notizen

Wird geladen…