Sodium Hydroxide → 4,5-Dibromobenzene-1,2-diamine

HRID 439457ノート

反応式

HRID 439457 の反応式
[Br:1][C:2]1[C:8]([Br:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[OH-].[Na+]>CCOC(C)=O>[Br:1][C:2]1[C:8]([Br:9])=[CH:7][C:5]([NH2:6])=[C:4]([NH2:10])[CH:3]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 127110274,5-Dibromo-2-nitroaniline

生成物 1

HCID 121969444,5-Dibromobenzene-1,2-diamine収率 97%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
75 °C

実験手順

To a solution of 4,5-dibromo-2-nitroaniline (3.35 g, 11.32 mmol) in EtOAc (150 mL) was added stannous chloride dihydrate (12.8 g, 56.74 mmol), the mixture was stirred at 75° C. for 16 h, then allowed to cool to room temperature and poured into ice-water (about 150 mL). To the mixture was added 1N aq NaOH with vigorous stirring to take the pH to 9 (pH paper). The resulting thick yellow white emulsion was extracted with EtOAc (3×100 mL). The organic extracts were combined, washed with brine (2×50 mL), dried (over Na2SO4) and evaporated to dryness. The residual solid was dried under 1 mmHg at 40° C. for 14 h giving 2.92 g (97%) of 4,5-dibromo-1,2-phenylenediamine as a yellowish powder. Mp 149°-50° C. IR (KBr) 3400, 1623, 1489, 1394, 1271, 868 cm-1. 1H NMR (DMSO-d6) 6.754 (s, 2H), 4.867 (s, 4H).

後処理

  1. temperatureto cool to room temperature
  2. stirringwith vigorous stirring
  3. extractionThe resulting thick yellow white emulsion was extracted with EtOAc (3×100 mL)
  4. washwashed with brine (2×50 mL)
  5. dry with materialdried (over Na2SO4)
  6. customevaporated to dryness
  7. customThe residual solid was dried under 1 mmHg at 40° C. for 14 h

出典と根拠

ORDレコード
ord-71974282c0cc43409a9c98be9271fbab
出典データセット
uspto-grants-1996_05
特許番号
US05514680

反応ノート

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