Cyclopropylamine → N-cyclopropyl-2-nitroaniline

Participants

Reaction Steps

To cyclopropylamine (27.3 g, 33.1 mL, 0.48 mol, 2.25 equiv; [CAS RN 765-30-0]) was added dropwise 2-fluoronitrobenzene (30.0 g, 0.21 mol, 1.0 equiv; [CAS RN 1493-27-2]) over 1 hours at 30° C. and stirring of the reaction mixture continued at room temperature for 18 h. The reaction mixture was extracted from a saturated aqueous solution of sodium bicarbonate (500 mL) with ethyl acetate (three times 300 mL) and the combined organic phases were dried over magnesium sulfate. Purification by silica gel column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a mixture of n-heptane:ethyl acetate (9:1) afforded 32.4 g (86%) of the title compound as a yellow oil. MS (ISP): m/z=178.0 [M+H]+.

Provenance & Evidence