2-Chloro-3-methylpyridine

colorless to light yellow liquid

Weighing 3-methylpyridine-2-carboxylic acid (56.7 mg, 0.3 mmol), sodium hydroxide (16.0 mg, 0.15 mmol), TBAC (26.3 mg, 0.45 mmol), DTBP (165 μL, 0.9 mmol) into 25 mL of Schlenk 25 mL of Schlenk, Then CH3CN (0.5 mL) was added and placed in a 50 °C oil bath for 20 h. After completion of the reaction, the solvent was removed under reduced pressure and eluted with petroleum ether / ethyl acetate.The solvent was separated on a silica gel column, The yield of 2-chloro-3-methylpyridine was 70percent.A 2-L flask was charged with 3-methyl-pyridine-N-oxide (3-PNO) (38.2 g, 0.35 mol), CH2C12 (742.0 g, 560 ml), and cooled to 0-5°C, 10percent of a solution of phosphorus oxychloride (POCl3) (107.4 g, 0.7 mol) in CH2C12 (93.3 g, 70 ml) was added to the flask. The remaining POCI3 solution and a solution of diisooctylamine (DIOA) (169.0 g, 0.7 mol) in cH2ci2 (92.8 g, 70 ml) were added to the flask over a 3 hour period at 0-5°C. The mixture was stirred for 2 hours at 0-5 °C. Water (105.2 g) was slowly added to the flask holding the temperature at or below 20°C. The mixture was stirred for 30 minutes then CH2CI2 was removed by distillation (600 ml) to a pot temperature of 67°C. The mixture was cooled to 25°C. 20percent NaOH solution (392.2 g) was added to the reaction mixture to a pH of 5.6. Water (101.4 g) was then added to the flask and the product was recovered by steam distillation. Conversion of 3-PNO = 99.9percent; crude product = 75.1 g; yield of 2C5MP = 14percent; ratio 2C5MP/2C3MP = 1.1/1A 2-L flask was charged with 3-PNO (38.2 g, 0.35 mol) and CH2C12 (742.3 g, 560 ml). Aluminum chloride (A1C13) (11.7 g, 0.088 mol) was added in portions to the flask. Exothermic reaction, solution addition was performed slowly. The mixture was cooled flask to 0-5° C. 10percent of a solution of P0C13 (107.3 g, 0.7 mol) in CH2C12 (93.3 g, 70 ml) was added to the flask at 0-5° C. The remaining P0C13 solution and a solution of diisopropylamine (71.0 g, 0.702 mol) in CH2C12 (92.8 g, 70 ml) were added co-currently to the flask at 0-5° C. The mixture was stirred at 0-5° C. for 2 hours, allowed to slowly warm to room temperature and stirred overnight. Water (105.0 g) was carefully added to the flask holding temperature at or below 35° C. The mixture was stirred 30 minutes. CH2C12 was removed by distillation to a pot temperature of 60° C. The mixture was cooled to 25° C. 20percent NaOH (416.2 g) was added to the reaction mixture to a pH of 5.0 while holding the temperature at or below 35°C. Conversion of 3-PNO=100percent; crude product=50.2 g; yield of 2C5MP=84.4percent; ratio 2C5MP/2C3MP=8.3/1

Molecular Weight:127.57
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Exact Mass:127.0188769
Monoisotopic Mass:127.0188769
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:74.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes