This is a scientific lab report prepared after an empirical observation. The main experiment is the synthesis of 1,4-Dihydropyridine. A simple dihydropyridine from a simple reactant (formaldehyde, ammonium acetate and 2,4-pentanedione ), is synthesized. The final part of this work deals with the determination of reasonable mechanisms for this synthesis.
1,4-Dihydropyridine is an equivalent of nicotinamide adenine dinucleotide (NADH) coenzymes. It exhibits a wide range of biological activities such as calcium channel blocking. This explains their wide use today in pharmacology.
The aim of this experiment is to synthesize a sample of dihydropyridine and determine the mechanisms for this synthesis.
- Formaldehyde (1, 3.0 mmol),
- 2,4-pentanedione (2, 9.0 mmol),
- Ammonium acetate (3, 12 mmol),
- Source of heat.
A mixture of formaldehyde (1, 3.0 mmol), 2,4-pentanedione (2, 9.0 mmol), and ammonium acetate (3, 12 mmol) in approximately 12 mL of water was heated at reflux for about 40 Minutes. The mixture was then cooled, filtered and washed with 10 – 15 mL of water. Washing was done for the second time with approximately equal amount of water as in the first case.
A pure solid product was obtained after washing. For confirmation on the purity of the solid substance, both IR and NMR spectrums, were obtained.
A melting point of approximately 2200 C was also obtained.
A recrystallization from absolute ethanol is done if any findings point towards an impure product.
In the analysis, the formaldehyde comes from 37% by weight solution. MW = 30 g/mol
2,4-pentanedione MW = 100 g/mol, Ammonium Acetate MW = 77 g/mol
The dihydropyridine is probably not (read not) very soluble in CDCl3 and therefore, use of DMSO/CDCl3 mixture for the NMR is employed.