Acetic Acid → HCID 87312636, compound

Participants

Reaction Steps

To a cold solution of 10 g (72.9 mmol) of p-aminobezoic acid (3) and 2.4 g (22.6 mmol) of sodium carbonate in 100 mL of DI water was added a solution of 3.5 g (50.7 mmol) of NaNO2 in 10 mL of DI water at 15° C. with stirring. The above mixture was poured into a mixture of 10 mL of concentrated HCl and 60 gm of crashed ice with stirring. Then of 11.2 g (73.2 mmol) of dimethoxyaniline (7) and 6 ml of acetic acid were added to the reaction mixture. After 10 min the reaction mixture was neutralized with 8 mL of 20% NaOH solution in water. The precipitant was filtered. Flash chromatography with chloroform/hexanes/acetone 5:3:2 mobile system provided 16 g (72.7%) of azo bezoate (8) as orange solid. TLC Rf 0.33 (1:9 MeOH-DCM). UV/Vis (methanol) λmax (nm) 450 (ε=31,800 M−1cm−1). 1H NMR (DMSO/D2O) δ 3.76 (s, 3H), 3.84 (s, 3H), 6.45 (s, 1H), 7.25 (s, 1H), 7.69 (d, 2H, J=8.4 Hz), 8.00 (d, 2H, J=8.4 Hz). ESMS 302.3 [C15H15N3O4 (M+H)+ requires 302.3].

Provenance & Evidence