Ethanol → 4-Fluoro-3-(morpholin-4-yl)aniline

Participants

Reaction Conditions

Reaction Steps

4-(2-Fluoro-5-nitro-phenyl)-morpholine (335.0 mg, 1.481 mmol) was dissolved in Ethanol (10.0 mL, 171 mmol) and the reaction was treated with Tin(II) chloride dihydrate (1671 mg, 7.405 mmol). The reaction was then heated at 70° C. until HPLC showed consumption of starting material. The mixture was then made basic with 10% NaOH and the product was extracted with ethyl acetate. Note: When adding the NaOH, solid precipitate formed and was filtered and washed with ethyl acetate. The solid was discarded and the combined organics were then washed with water and dried over sodium sulfate, filtered and reduced to afford 235 mg of 4-Fluoro-3-morpholin-4-yl-phenylamine. 1H NMR (400 MHz, DMSO, d6) δ 6.75 (m, 1H), 6.21 (d, 1H, J=7.56 Hz), 6.10 (m, 1H), 4.84 (s, 2H), 3.70 (m, 4H), 2.92 (m, 4H).

Provenance & Evidence