Sulfuric Acid → 3-Chloro-5-ethylnitrobenzene

HRID 326639

反応式

HRID 326639 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 197352173-Chloro-5-ethylnitrobenzene

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0fe94976548c40f0a9b7b208c3adf67c
出典データセット
uspto-grants-1993_12
特許番号
US05270309

関連ノート

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