Sodium Carbonate → 4-Bromo-3-chlorobenzene-1,2-diamine

HRID 913564ノート

反応式

HRID 913564 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[C:3]=1[Cl:12].C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[Br:1][C:2]1[C:3]([Cl:12])=[C:4]([NH2:9])[C:5]([NH2:6])=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 10340Sodium CarbonateHCID 265991564-Bromo-3-chloro-2-nitroaniline

生成物 1

HCID 578001544-Bromo-3-chlorobenzene-1,2-diamine収率 96.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

To a stirred solution of 4-bromo-3-chloro-2-nitroaniline (0.200 g, 0.797 mmol) in EtOH (100 mL), was added SnCl2-2H2O (0.9 g, 3.985 mmol). The reaction mixture was heated to reflux for 3.5 h. The cooled solution (to rt) was diluted with H2O and the pH was adjusted to ca. 10 with Na2CO3. Extraction with CHCl3 (×3), was followed by washing with brine, drying over Na2SO4, and filtration. Concentration afforded an orange solid that was dried under vacuum to obtain 0.17 g product: 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.90 (s, 2H), 3.40 (s, 2H); MS (ESI) m/z 223 (M+1).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3.5 h
  3. extractionExtraction with CHCl3 (×3)
  4. washby washing with brine
  5. dry with materialdrying over Na2SO4, and filtration
  6. concentrationConcentration
  7. customafforded an orange solid
  8. customthat was dried under vacuum

出典と根拠

ORDレコード
ord-e6a1289e03824bbaaddea45adad8311d
出典データセット
uspto-grants-2011_09
特許番号
US08026262B2

反応ノート

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