Hydrochloric Acid → HCID 87312380, compound

Participants

Reaction Steps

To a cold solution of 10 g (72.9 mmol) of p-aminobezoic acid 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 10.8 g (62.4 mmol) of 1,3,3-trimethyl-2-methyleneindoline 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 7.3 g (31.1%) of azo bezoate (2) as orange solid. TLC Rf 0.26 (chloroform/hexanes/acetone 5:3:2). UV/Vis (methanol) λmax (nm) 455 (ε=32,600 M−1cm−1). ESMS 322.3 [C19H19N3O2 (M+H)+ requires 322.4].

Provenance & Evidence