Lithium Hydroxide → HCID 24075694, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4-fluoro-3-nitrobenzoate (Chontech 01072; 500 mg; 2.35 mmol; 1 eq.) and N-methylcyclohexylamine (Aldrich 10, 332-2; 796.59 mg; 7.04 mmol; 3 eq.) in DMF (2 mL) was stirred at 50° C. for 3 hours. The reaction was then allowed to return to room temperature and diluted with water. Extraction with ethyl acetate, drying over sodium sulfate and concentration in vacuo gave a yellow oil. The oil was taken up in THF (15 mL) and lithium hydroxide (280.86 mg; 11.73 mmol; 5 eq.) was added followed by water (15 mL). The reaction mixture was stirred at room temperature for 5 hours. After evaporation of the solvent, the solution was diluted with water and washed with Et2O. The aqueous layer was acidified to pH 4 with AcOH, extracted with Et2O, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a yellow solid.

Provenance & Evidence