Sodium Iodide → 3-(4-Iodophenyl)pyridine

HRID 256842

反応式

HRID 256842 の反応式
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

参加物

8

反応物 5

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

生成物 1

HCID 126443563-(4-Iodophenyl)pyridine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

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°.

後処理

  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°

出典と根拠

ORDレコード
ord-522ca747e8864b26bb6333b54e87b500
出典データセット
uspto-grants-1993_11
特許番号
US05260294

関連ノート

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