Reaction #62691

Reaction equation

2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine

thionyl chloride

3-bromopropanol

→

2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine

Solvents

CH2Cl2

DMF

Conditions

Workup

1. 1
   Temperaturecooled to 5° C
2. 2
   workup.STIRRINGthe solution stirred for 1 hour at room temperature
3. 3
   WashThe solution was then washed with water
4. 4
   Dryingthe organic layer dried over sodium sulfate
5. 5
   Otherevaporated under reduced pressure
6. 6
   OtherThe product was recrystallized from ethyl acetate

Procedure

A solution of 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-carboxy-1,4-dihydropyridine (107 g, 0.32 mol) in CH2Cl2 (520 mL) and DMF (100 mL) was cooled to 0° C. and thionyl chloride (28 mL, 0.39 mol) slowly added. The mixture was stirred at room temperature for 1 hour, then cooled to 5° C. Distilled 3-bromopropanol (35 mL, 3.9 mol) was slowly added, and the solution stirred for 1 hour at room temperature. The solution was then washed with water and the organic layer dried over sodium sulfate and evaporated under reduced pressure. The product was recrystallized from ethyl acetate to yield 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(3-bromopropoxycarbonyl)-1,4-dihydropyridine (12, mp=146° C.).

Source