Reaction #6006

Reaction equation

2-chloro-3-cyclopentylidenemethylquinoline

sodium hydroxide

→

3-cyclopentylidenemethylquinoline

Yield 99.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was cooled
2. 2
   Otherbeing kept below 20° C.
3. 3
   ExtractionThe resulting mixture was then extracted with ethyl acetate (2×250 ml)
4. 4
   DryingThe combined organic extracts were dried over sodium sulphate
5. 5
   Concentrationthen concentrated in vacuo (30° C., 14 mmHg)
6. 6
   Otherto give a crude red oil (8 g) which
7. 7
   Extractionwas extracted with hot pentane (2×200 ml)

Procedure

A solution of 2-chloro-3-cyclopentylidenemethylquinoline (7.6 g, 31.3 mmol) in glacial acetic acid (80 ml) at 60° C. was treated with zinc powder (4.0 g, 62.6 mmol). After stirring at 60° C. for 3 hours, the reaction mixture was cooled and then treated dropwise with aqueous sodium hydroxide solution (2M, 330 ml); the temperature being kept below 20° C. throughout. The resulting mixture was then extracted with ethyl acetate (2×250 ml). The combined organic extracts were dried over sodium sulphate then concentrated in vacuo (30° C., 14 mmHg) to give a crude red oil (8 g) which was extracted with hot pentane (2×200 ml). Concentration of the combined extracts in vacuo (20° C.; 14 mmHg) afforded 3-cyclopentylidenemethylquinoline (4 g, 31 mmol) which was used without further purification;

Source