2-CHLORO-1-METHYLPYRIDINIUM P-TOLUENESULFONATE synthesis

Yield: 88%

Reaction Conditions:

at 80 - 85; for 1 h;

Steps:

A Preparation of 2-chloro-N-methylpyridinium tosylate
In a 25 ml round-bottomed flask topped with a condenser, 2-chloropyridine (2.3 g, 20.6 mmol) and methyl tosylate (3.83 g, 20.6 mmol) were heated at 80-85° C. for one hour.Hot toluene (15 ml) was then added before the mixture was cooled and crystallized.The whole mixture was left stirring for 10 minutes and the mixture was left to return to room temperature.The crystallized bottom phase was recovered.The product was in the form of a white solid and was obtained with a yield of 88% (5.4 g).The NMR characteristics were the following:¹H NMR (300 MHz, CDCl₃): 2.26 (s, 3H); 4.35 (s, 3H); 7.04 (d, J=8 Hz, 2H); 7.56 (d, J=8 Hz, 2H); 7.85-7.91 (m, 2H); 8.38-8.44 (m, 1H); 9.34 (d, J=5.3 Hz, 1H).¹³C NMR (75 MHz, CDCl₃): Primaries: 21.3; 47.8. Secondaries: - Tertiaries: 125.7; 126.7 (2C); 128.8 (2C); 129.5; 149.6; 154.5. Quaternaries: 140.1; 143.4; 147.4.

References:

Rhodia Chimie;CNRS US2009/234151, 2009, A1 Location in patent:Page/Page column 7