Sodium Hydroxide → HCID 19095337, compound

Participants

Reaction Steps

N-[2-[3-Methyl-2-phenylpyrrol-1-yl]ethyl]acetamide (2.6 g) was treated with 20 ml of phosphorus oxychloride under argon and boiled under reflux for 1 hour. 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 (1×300 ml, 2×150 ml). The organic extracts were combined, washed once with 100 ml of water, dried with MgSO4 and freed from solvent. 2.1 g of crude product were dissolved in a 25-fold amount of ethanol at the boiling temperature and treated with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. After the addition of 50 ml of ethyl acetate 2.0 g of pale yellow crystals separated and were recrystallized from ethyl acetate/ethanol (1:1). There were obtained 1.3 g (30%) of 3,4-dihydro-1,7-dimethyl-6-phenylpyrrolo[1,2-a]pyrazine fumarate (2:3); m.pt.: 157°-159° C. (dec.).

Provenance & Evidence