Sodium Hydroxide → 1-(4-Chloro-3-fluorophenyl)-2-methylpropan-2-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(1-(4-chloro-3-fluorophenyl)-2-methylpropan-2-yl)acetamide (3.36 g, 13.80 mmol) and concentrated hydrochloric acid (60 mL) was heated at 120° C. for 16.5 h. The mixture was cooled to rt and poured into ice water and the resulting mixture was adjusted to pH>12 with NaOH and extracted with EtOAc (80 mL×5). The combined organic phases were washed with brine (100 mL×2), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The residue was dissolved in concentrated hydrochloric acid (60 mL) and the mixture was stirred at 120° C. for 20 h. The reaction mixture was cooled to rt and 100 mL of water was added. The resulting mixture was washed with EtOAc (50 mL×3). The aqueous phase was adjusted to pH>11 with NaOH and extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (80 mL×2), dried over anhydrous Na2SO4 (20 g) and concentrated in vacuo to give the tile compound as a yellow solid (0.484 g, 17.4%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence