Acetic Acid → 2-Chloro-5-ethylpyridine

HRID 129101Notes

Reaction equation

HRID 129101 reaction equation
[N:1]1([CH:6]=[CH:7][C:8]#N)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1(C=CCC)CCCC1.C(O)(=O)C.[ClH:23]>C(Cl)(Cl)Cl>[Cl:23][C:6]1[CH:7]=[CH:8][C:4]([CH2:3][CH3:2])=[CH:5][N:1]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1396491-But-1-enylpyrrolidineHCID 12732581beta-Pyrrolidino-acrylonitrile

Product 1

HCID 111263632-Chloro-5-ethylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

19.3 g of β-pyrrolidino-acrylonitrile were added at -10° C. to 30 g of pyrrolidino-butene from A4 in 50 ml of chloroform. The mixture was allowed to warmto RT, and 50 ml of acetic acid were added dropwise. After stirring at RT for 15 hours, the mixture was cooled to -10° C., and dry hydrogen chloride gas was introduced. Aqueous workup gave 2-chloro-5-ethylpyridine as the main product.

Workup

  1. customto warmto RT
  2. temperaturethe mixture was cooled to -10° C.

Sources & evidence

ORD record
ord-14b569afbedf4364a9df29d744aacb65
Source dataset
uspto-grants-1995_11
Patent number
US05466800

Reaction notes

Loading…