Hydrochloric Acid → 2-Chloro-3-hydroxy-6-iodopyridine

HRID 387835

反応式

HRID 387835 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[I-:9].[Na+].CC1C=CC(S(NCl)(=O)=O)=CC=1.Cl>CN(C)C=O.CCCCCC.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 31388TosylchloramideHCID 811362-Chloro-3-pyridinol

生成物 1

HCID 107774172-Chloro-3-hydroxy-6-iodopyridine収率 91.2%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

After dissolving 2-chloro-3-hydroxypyridine (5.00 g, 38.6 mmol) and sodium iodide (5.79 g, 38.6 mmol) in dimethylformamide (70 ml), Chloramine T (10.9 g, 38.6 mmol) was added while cooling on ice, and then the mixture was stirred at room temperature for 1 hour. Upon adding 2N aqueous hydrochloric acid (19.3 ml, 38.6 mmol) after the reaction, the reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:hexane=1:2), and the fraction containing the target substance was concentrated to obtain the title compound (9.00 g, 35.2 mmol, 91%) as colorless crystals.

後処理

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. customafter the reaction
  4. washthe organic layer was washed with water and saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationthe drying agent was filtered off
  7. distillationthe filtrate was distilled off under reduced pressure
  8. customThe obtained crude product
  9. additionthe fraction containing the target substance
  10. concentrationwas concentrated

出典と根拠

ORDレコード
ord-8aaf834e55664c51bfd51805daae7681
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

関連ノート

読み込み中…