Ethanol → HCID 54691690, compound

Participants

Reaction Steps

The title compound was prepared by the general method of Southwick [J. Org. Chem. 21, 1087 (1956)]. Thus to a solution of n-pentylamine (8.04 g, 92.3 mmol) in 50 ml of dry EtOH was added ethyl acrylate (9.24 g, 92.3 mmol) with stirring under nitrogen at room temperature. After 18 h at room temperature, diethyl oxalate (13.5 g, 92.3 mmol) was added followed by a solution of sodium ethoxide in EtOH [made from sodium (2.12 g, 92.3 mmol) in 50 ml of dry EtOH]. The reaction mixture was then heated under reflux for 1 hour. To the resulting suspension was added 150 ml H2O and the reaction mixture was then concentrated under a stream of nitrogen to remove the EtOH. The white solid was then dissolved in 200 ml H2O and the solution was acidified with concentrated aqueous HCl (8.9 ml of a 10.4N solution). The resulting crystals were filtered, washed with water and dried to give the title compound (15.9 g, 71.4%) as colorless plates: mp 122°-123° C. Anal calcd for C12H19NO4 : C, 59.74; H, 7.94; N, 5.80. Found: C, 59.46; H, 7.87; N, 5.83.

Provenance & Evidence