Reaction #1687630

Reaction equation

nicotinic acid

methyl glycinate hydrochloride

dicyclohexylcarbodiimide

p-toluenesulfonic acid

→

77

N-Methoxycarbonylmethyl-nicotinamide

Solvents

water

pyridine

Conditions

Workup

1. 1
   FiltrationFiltration and evaporation in vacuo
2. 2
   Othergave a heavy oil which
3. 3
   ExtractionAfter basification with ammonia the aqueous solution was extracted with 3×300 ml of dichloromethane
4. 4
   DryingThe organic phase was dried over magnesium sulphate, and removal of the solvent in vacuo

Procedure

A mixture of 50.0 g (0.400 mol) of nicotinic acid, 50.0 g (0.400 mol) of methyl glycinate hydrochloride, 90 g (0.440 mol) of dicyclohexylcarbodiimide, and 2 g of p-toluenesulfonic acid in 500 ml of dry pyridine was stirred overnight at room temperature. Filtration and evaporation in vacuo gave a heavy oil which was dissolved in 500 ml of water. After basification with ammonia the aqueous solution was extracted with 3×300 ml of dichloromethane. The organic phase was dried over magnesium sulphate, and removal of the solvent in vacuo gave crude 77 as a heavy yellow oil. Yield: 63.0 g (0.320 mol, 81%).

Source