p-Toluenesulfonic acid → HCID 178439035, compound

Participants

Reaction Conditions

Reaction Steps

Prepare a mixture of the 2-formyl-6-bromopyridine (72 g, 0.38 mol) of Step (a) and 2,6-diisopropylaniline (73 g, 0.38 mmol) in 500 mL of anhydrous toluene containing 0.3 nanometer (nm) pore size molecular sieves (6 g) and 80 mg of 4-methylbenzenesulfonic acid (p-TsOH) to give a mixture. Add the mixture to a dry, 500 mL 3-neck round bottom flask equipped with a condenser, an overhead mechanical stirrer, and a thermocouple well. Heat the mixture to 70° C. under a nitrogen gas atmosphere and stir for 12 hours. Cool the mixture to room temperature, filter it, and remove volatiles under reduced pressure until a constant weight to give the 6-bromo-2-(2,6-diisopropylphenyl)iminopyridine as a brown oil. Yield is 0.11 kg (82%). GC/MS 346 (M+), 331, 289, 189, 173, 159, 147, 131, 116, 103, 91, 78. Use the 6-bromo-2-(2,6-diisopropylphenyl)iminopyridine without further purification in step (c) below.

Provenance & Evidence