Reaction #1583871

Reaction equation

water

Quinidine

5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Quinidine

→

(R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Yield 18.6%

Solvents

methanol

Conditions

Workup

1. 1
   workup.DISSOLUTIONwas completely dissolved
2. 2
   workup.WAITThe stirring was continued for 0.5 hour
3. 3
   TemperatureThe mixture was cooled down slowly
4. 4
   OtherA solid was precipitated out and
5. 5
   Filtrationwas filtered
6. 6
   workup.ADDITIONThe filter cake was treated with hydrochloric acid

Procedure

To a solution of 5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (700 g, 2.1 mol) in methanol (14 L) was added Quinidine (617 g, 1.90 mol). The mixture was stirred at 90° C. under reflux until Quinidine was completely dissolved. The stirring was continued for 3 hours. 4.5 L water was added. The stirring was continued for 0.5 hour. The mixture was cooled down slowly. A solid was precipitated out and was filtered. The filter cake was treated with hydrochloric acid to produce (R)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (130 g) in a yield of 18.6%.

Source