Sodium Iodide → HCID 86752384, compound

Participants

Reaction Steps

4'-(2-Hydroxy-3-methoxybenzylamino)acetophenone (500 mg, 1.84 mmol) is treated with 629 mg (3.22 mmol) of ethyl 4-bromobutyrate, 764 mg (5.53 mmol) of potassium carbonate and a catalytic amount (182 mg, 1.22 mmol) of sodium iodide in 2 mL N,N-dimethylformamide as described in Preparation 3 to give 680 mg of 4-[2-[[(4-acetylphenyl)amino]methyl]-6-methoxyphenoxy]butanoic acid, ethyl ester as a light brown oil (95%). The 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 3400, 1730, 1660, 1600 cm-1 ; MS (CI) m/e 386 (M+H), 115; Analysis calculated for C22 H27O5N: C, 68.55; H, 7.06; N, 3.63; found: C, 68.27; H, 6.81; N, 3.54.

Provenance & Evidence