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

HRID 60226

반응식

HRID 60226 반응식
[Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([NH2:8])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 4875Potassium IodideHCID 661742-Amino-5-chloropyridineHCID 23665710Potassium Iodate

생성물 1

HCID 110760102-Amino-5-chloro-3-iodopyridine수율 169.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

반응 조건

온도
100 °C

실험 절차

A stirred solution of 5-chloro-pyridin-2-ylamine (51.4 g, 0.40 mol) in 2M sulfuric acid (700 mL) was treated portionwise with potassium iodate (43.7 g, 0.2 mol) and the mixture heated to 100° C. A solution of potassium iodide (36.5 g, 0.55 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 tan solid (86.3 g, 84%). LCMS (Method B): RT=3.76 min, M+H+=255/257. 1H NMR (400 MHz, CDCl3): 7.98 (d, J=2.3 Hz, 1H), 7.84 (d, J=2.3 Hz, 1H), 5.03 (s, 2H).

후처리

  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

출처 및 근거

ORD 기록
ord-8bee69c3c77846cd9d59d0b132710ef9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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