Sodium Hydroxide → HCID 19095408, compound

Participants

Reaction Steps

N-[2-(2-p-Tolylpyrrol-1-yl)ethyl]acetamide (3.9 g) was treated with 20 ml of phosphorus oxychloride under argon and boiled for 1/2 hour while stirring. The reaction mixture was hydrolyzed at 0° C. with 100 ml of 2N sodium hydroxide solution and 100 ml of 28% sodium hydroxide solution, diluted with 1000 ml of water and extracted with methylene chloride (1×200 ml, 2×100 ml). The organic extracts were combined, dried with MgSO4 and freed from solvent. 1.7 g of a total of 3.5 g of crude product were dissolved in a 25-fold amount of ethanol and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 1.8 g (68%) of 3,4-dihydro-1-methyl-6-p-tolylpyrrolo[1,2-a]pyrazine fumarate (1:1); m.pt.: 186°-189° C. (dec.).

Provenance & Evidence