Reaction #62689

Reaction equation

2-cyanoethy 3-oxobutanoate

methyl 3-aminocrotonate

3-nitrobenzaldehyde

→

racemic 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-cyano)ethoxycarbonyl-1,4-dihydropyridine

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 8 hours
3. 3
   FiltrationThe resulting precipitate was filtered
4. 4
   Washwashed with methanol
5. 5
   Otherdried

Procedure

A mixture of 2-cyanoethy 3-oxobutanoate (83.3 g, 0.54 mol), methyl 3-aminocrotonate (61.9 g, 0.54 mol), and 3-nitrobenzaldehyde (81.3 g, 0.54 mol) in methanol (540 mL ) was heated at reflux for 8 hours, then stirred overnight. The resulting precipitate was filtered, washed with methanol, and dried to produce racemic 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-cyano)ethoxycarbonyl-1,4-dihydropyridine (mp=123° C.).

Source