Chloroacetone → 2-Methylindolizine

Temperature

20 °C

A mixture of 92.5 g monochloroacetone (1 mole) and 93 g of α-picoline (1 mole) was heated for 21/2 h on a boiling water-bath. The reaction mixture was cooled to ambient temperature (20° C.) and kept overnight. A solid black mass formed. Extraction was performed on a hot water-bath until the mass had dissolved completely (about 700 ml). The solution was filtered and washed 3 times with 100 ml of ether. A few ml of an aqueous saturated sodium carbonate solution were added and the solution was then washed again 4 times in ether. 150 g of solid sodium hydrogen carbonate was added carefully and steam distillation was carried out. The distillate was cooled and sucked off. The solid product was dissolved quickly in ether and dried on heated magnesium sulphate. The ether was evaporated and the residue dried.

1. temperaturewas heated for 21/2 h on a boiling water-bath
2. customA solid black mass formed
3. extractionExtraction
4. customwas performed on a hot water-bath until the mass
5. dissolutionhad dissolved completely (about 700 ml)
6. filtrationThe solution was filtered
7. washwashed 3 times with 100 ml of ether
8. additionA few ml of an aqueous saturated sodium carbonate solution were added
9. washthe solution was then washed again 4 times in ether
10. addition150 g of solid sodium hydrogen carbonate was added carefully
11. distillationsteam distillation
12. temperatureThe distillate was cooled
13. dissolutionThe solid product was dissolved quickly in ether
14. customdried
15. temperatureon heated magnesium sulphate
16. customThe ether was evaporated
17. customthe residue dried

ORD record

ord-f1cc5c6a19c443cdb9f822a4157f3d5a

Source dataset

uspto-grants-1980_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04202697