Hydrogen Bromide → Cotinine

HRID 55545

反応式

HRID 55545 の反応式
[N:1]1[CH:6]=[C:5]([CH:7]2[CH2:12][CH2:11][CH2:10][N:8]2[CH3:9])[CH:4]=[CH:3][CH:2]=1.[Br-].[Na+].Br.Br([O-])(=O)=[O:17].[Na+].BrBr.Cl>[Zn].C(O)(=O)C>[CH3:9][N:8]1[C:10](=[O:17])[CH2:11][CH2:12][C@H:7]1[C:5]1[CH:4]=[CH:3][CH:2]=[N:1][CH:6]=1

参加物

9

反応物 6

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 9423-(1-Methylpyrrolidin-2-yl)pyridineHCID 24408BromineHCID 253881Sodium BromideHCID 23668195Sodium Bromate

生成物 1

HCID 854019Cotinine

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

The invention will be better understood by reference to the FIGURE which illustrates the invention by way of example. As shown in the FIGURE, nicotine together with an alkali metal bromide, e.g., sodium bromide or hydrogen bromide, and an alkali metal bromate, e.g., sodium bromate, was placed in an aqueous solution in a reactor and heated in the presence of an acid, e.g., hydrochloric and acetic acids. The red color produced in the reactor indicated the presence of elemental bromine. A red-orange precipitate of dibromocotinine hydrobromide perbromide was then separated and collected by suction filtration. This intermediate product was then kept in the same reactor or, if desired, isolated and placed in a second reactor. The intermediate product is mixed with an acid, e.g., acetic acid and hydrochloric acid, followed by the addition of zinc dust or granules. The zinc was removed by suction filtration and the resulting cotinine was extracted with an organic solvent, e.g., chloroform. Finally, the extract was concentrated by evaporation to produce cotinine as a brown, viscous liquid. Analysis by thin-layer chromatography (TLC) showed that the material collected was about 95% cotinine with norcotinine as a by-product with a trace of nicotine present.

後処理

  1. temperatureheated in the presence of an acid, e.g.
  2. customThe red color produced in the reactor
  3. customA red-orange precipitate of dibromocotinine hydrobromide perbromide was then separated
  4. filtrationcollected by suction filtration
  5. customisolated
  6. customplaced in a second reactor
  7. customThe zinc was removed by suction filtration
  8. extractionthe resulting cotinine was extracted with an organic solvent, e.g., chloroform
  9. concentrationFinally, the extract was concentrated by evaporation

出典と根拠

ORDレコード
ord-b9495280550f4a72a72bf094d4d47f09
出典データセット
uspto-grants-1997_04
特許番号
US05625070

関連ノート

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