Sodium Iodide → 3-(4-Iodophenyl)pyridine

HRID 256842노트

반응식

HRID 256842 반응식
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.N([O-])=O.[Na+].[I-:25].[Na+].C([O-])(=O)C.[Na+]>O.C(O)(=O)C>[I:25][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 4595224-(Pyridin-3-yl)anilineHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

생성물 1

HCID 126443563-(4-Iodophenyl)pyridine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

A mixture of 1.7 g (10 mmol) of 3-(4-aminophenyl)-pyridine [F. S. Tanaka et al., J. Agric. Food Chem. 30, 957 (1982)], 17 ml of glacial acetic acid and 1.5 ml of trifluoroacetic acid was cooled in ice-water. Sodium nitrite, 0.8 g (11.4 mmol) was added in portions. After stirring for 15 minutes in ice-water and 15 minutes without cooling, 5 g of sodium iodide and 3 g of sodium acetate was added slowly with water cooling. The reaction mixture was diluted with 30 ml of water and stirred for 30 minutes. It was then partitioned between methylene chloride and 10% aqueous sodium carbonate solution. The organic phase was dried and evaporated and the residue was chromatographed over 20 g of silica gel using 10% (V/V) of ethyl acetate in methylene chloride. Crystallization from hexane yielded off-white crystals with m.p. 112°-115°.

후처리

  1. temperaturewithout cooling
  2. customIt was then partitioned between methylene chloride and 10% aqueous sodium carbonate solution
  3. customThe organic phase was dried
  4. customevaporated
  5. customthe residue was chromatographed over 20 g of silica gel using 10% (V/V) of ethyl acetate in methylene chloride
  6. customCrystallization from hexane yielded off-white crystals with m.p. 112°-115°

출처 및 근거

ORD 기록
ord-522ca747e8864b26bb6333b54e87b500
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260294

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