Potassium Iodide → 2-Amino-5-fluoro-3-iodopyridine

HRID 60218

反応式

HRID 60218 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[I:9]([O-])(=O)=O.[K+].[I-].[K+]>S(=O)(=O)(O)O.O>[F:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([NH2:8])=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 4875Potassium IodideHCID 27377012-Amino-5-fluoropyridineHCID 23665710Potassium Iodate

生成物 1

HCID 184559742-Amino-5-fluoro-3-iodopyridine収率 116.9%

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 stirred solution of 5-fluoro-pyridin-2-ylamine (50 g, 0.45 mol) in 2M sulfuric acid (250 mL) was treated portionwise with potassium iodate (48 g, 0.22 mol) and the mixture heated to 100° C. A solution of potassium iodide (41 g, 0.24 mol) in water (100 mL) was added dropwise over ca. 1 hour. The mixture was allowed to stir for a further 30 minutes then cooled to ambient temperature. The pH of the aqueous phase was adjusted to 8-9 and the mixture extracted with ethyl acetate (×3). The combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine, dried (Na2SO4), filtered and evaporated to afford the title compound as a yellow solid (61.2 g, 58%). 1H NMR (400 MHz, CDCl3): 7.94 (d, J=2.7 Hz, 1H), 7.68 (dd, J=7.2, 2.7 Hz, 1H), 4.85 (s, 2H).

後処理

  1. temperaturethen cooled to ambient temperature
  2. extractionthe mixture extracted with ethyl acetate (×3)
  3. washThe combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-ee5df0ba6ae1490c9a8d79ee19b04bd0
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

関連ノート

読み込み中…