Potassium Iodide → 2-Amino-3-iodo-5-nitropyridine

HRID 1515844

反応式

HRID 1515844 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[I:11]([O-])(=O)=O.[K+].[I-].[K+].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O.O>[NH2:1][C:2]1[C:7]([I:11])=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 778882-Amino-5-nitropyridineHCID 516892Sodium BicarbonateHCID 23665710Potassium Iodate

生成物 1

HCID 116231122-Amino-3-iodo-5-nitropyridine収率 134.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-amino-5-nitropyridine (86.3 g, 0.625 mol) and potassium iodate (53.5 g, 0.25 mol) in 2 M sulfuric acid was heated at 100° C. and a solution of potassium iodide (100 g, 0.603 mol) in water (250 mL) was added dropwise over 1 h. The resulting brown mixture was refluxed for 12 h. After being cooled to room temperature, the mixture was adjusted to pH 7 by careful addition of solid sodium bicarbonate. The mixture was extracted with dichloromethane, washed with a saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, and the solvent removed in vacuo to afford 2-amino-3-iodo-5-nitropyridine (89.3 g, 60%) as a yellow solid: LC/MS m/e calcd for C5H4IN3O2 [M+H]+ 266.01, observed 266.

後処理

  1. temperatureThe resulting brown mixture was refluxed for 12 h
  2. temperatureAfter being cooled to room temperature
  3. extractionThe mixture was extracted with dichloromethane
  4. washwashed with a saturated sodium thiosulfate solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-836b9a9017ec42e29a7e7150bc983324
出典データセット
uspto-grants-2012_07
特許番号
US08222416B2

関連ノート

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