Sulfuric Acid → HCID 69853761, compound

Participants

Reaction Steps

15.5g (0.1 mole) 2-fluoro-5-nitrotoluene, 25 ml (0.3 mole) pyrrolidine, 11.0 g Na2CO3 were combined with 50 ml 2-ethoxyethanol and refluxed with stirring. When the TLC showed no evidence of starting material (ca. 2 hours), the mixture was poured onto ice. The precipitate was filtered, washed 5 times with cold H2O, and dried on filter paper for 2 hours. The resulting solid was mixed with 125 ml 2-propanol, 10% Pd/C, and hydrogenated at 60 psi on a Parr apparatus. The mixture was filtered through filter-aid and stirred with external cooling in an ice/acetone bath. A cold solution of 10.7 g (0.105 mole) concentrated H2SO4 in 15 ml 2-propanol was added dropwise over 15 minutes. The resultant precipitate was filtered, washed 2 times with 2-propanol and dried in vacuo at 50° C. The final yield was 24.45 g (89%) of a light grey solid. MS (solid probe): m/e 176 (free base).

Provenance & Evidence