Hydrochloric Acid → HCID 87312933, compound

Participants

Reaction Steps

To a cold solution of 5 g (16.6 mmol) of 4-(4-carboxy-phenylazo)-2,5-dimethoxyaniline (8) and 1.25 g (11.8 mmol) of sodium carbonate in 50 mL of DI water was added a solution of 1.75 g (25.4 mmol) of NaNO2 in 5 mL of DI water at 15° C. with stirring. The above mixture was poured into a mixture of 5 mL of concentrated HCl and 30 gm of crashed ice with stirring. Then of 2.9 g (16.6 mmol) of 1,3,3-trimethyl-2-methyleneindoline and 1.5 ml of acetic acid were added to the reaction mixture. After 10 min the reaction mixture was neutralized with 6 mL of 20% NaOH solution in water. The precipitant was filtered. Flash chromatography with chloroform/hexanes/acetone 5:3:2 mobile system provided 5.5 g (68.2%) of azo bezoate (9) as dark blue solid. TLC Rf 0.48 (1:9 MeOH-DCM). UV/Vis (buffer pH=11) λmax (nm) 585 (ε=48,500 M−1cm−1). 486.6 [C27H27N5O4 (M+H)+ requires 486.5].

Provenance & Evidence