Iodine → 6-Chloro-2-iodopyridin-3-amine

HRID 513063

반응식

HRID 513063 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[I:9]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[Cl:1][C:2]1[N:7]=[C:6]([I:9])[C:5]([NH2:8])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 807IodineHCID 793055-Amino-2-chloropyridine

생성물 1

HCID 184070436-Chloro-2-iodopyridin-3-amine수율 86.4%

시약·촉매·용매 2

HCID 159865Silver sulfate촉매HCID 702Ethanol용매

반응 조건

온도
20 °C

실험 절차

To a solution of 6-chloro-pyridin-3-ylamine (10.0 g, 77.8 mmol) in EtOH (150 mL) was added Ag2SO4 (12.1 g, 38.9 mmol) and I2 (23.7 g, 93.4 mmol) at room temperature. The mixture was stirred at 20° C. overnight. The solvent was removed by evaporation under vacuum. Water (100 mL) and EtOAc (200 mL) were added to the residue. The organic layer was separated and the aqueous layer was extracted with EtOAc (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1) to give 6-chloro-2-iodo-pyridin-3-ylamine (17.1 g, 86%). 1H NMR (DMSO, 300 MHz) δ 7.16 (d, J=8.4 Hz, 1H), 7.01 (d, J=8.4 Hz, 1H), 5.57 (s, 2H).

후처리

  1. customThe solvent was removed by evaporation under vacuum
  2. additionWater (100 mL) and EtOAc (200 mL) were added to the residue
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (100 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. customto give the crude product, which
  8. customwas purified by column chromatography on silica gel (Petroleum ether/Ethyl acetate 7:1)

출처 및 근거

ORD 기록
ord-df791a2e39074c7ca9e7896999ccfcac
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102672B2

연결된 노트

불러오는 중…