Reaction #83823

Reaction equation

nicotine

sodium bromate

sodium bromide

hydrogen bromide

bromine

hydrochloric acid

→

cotinine

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperatureheated in the presence of an acid, e.g.
2. 2
   OtherThe red color produced in the reactor
3. 3
   OtherA red-orange precipitate of dibromocotinine hydrobromide perbromide was then separated
4. 4
   Filtrationcollected by suction filtration
5. 5
   Otherisolated
6. 6
   Otherplaced in a second reactor
7. 7
   OtherThe zinc was removed by suction filtration
8. 8
   Extractionthe resulting cotinine was extracted with an organic solvent, e.g., chloroform
9. 9
   ConcentrationFinally, the extract was concentrated by evaporation

Procedure

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.

Source