Sulfuric Acid → 3-Chloro-5-ethylnitrobenzene

HRID 326639

반응식

HRID 326639 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 197352173-Chloro-5-ethylnitrobenzene

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0fe94976548c40f0a9b7b208c3adf67c
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05270309

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