Screening approach to the Reissert reaction

29 Jan
Published by Michael Wolfle

 
General procedure
 
Freshly distilled isoquinoline (1.28 mmol, 165 mg), potassium cyanide (3.84 mmol, 250 mg) and the various additives (see Table 1) were solved in a mixture of DCM (10 mL) and water (5 mL) and tempered according the conditions given in Table 2. A solution of cyclohexanoyl chloride (1.28 mmol, 165 mg, 150 µL) in DCM (2 mL) was added over a period of 30 min to the vigorously stirred reaction mixture. After the time given in Table 2 the organic layer was separated, washed with water and brine and dried over magnesium sulfate. The solution was filtered over silica gel and concentrated under reduced pressure. Then the yellowish to brownish reaction mixture was prepared for further analytics.
 
 

Table 1. Additives to the reaction mixture
 
 
Table2
Table 2. Reaction conditions                                         a) phase transfer catalyst


 
Reaction control by TLC:
TLC1TLC2TLC3
(TLC conditions: hexane:EA = 1:1; stain: KMnO4)