With this AZO dyes coupling reaction I did it many times, but did not work at al

Question

With this AZO dyes coupling reaction I did it many times, but did not work at all my question is : when they said until the mixture become homogenous what should looks like ? Is it nessery to stir this mixture (aniline +H2O+HCL ) before cool it down ? What about alkhole as solvent should be hydrous or anhydrous ? Why ? This rxn should run under N2 gas or not ? Why ? Any other notice or recommendation that could be helpful for this rxn to try make it rightly ! C a suspension of 4-bromoaniline (1.37 g, 7.96 mmol) in water (10 mL). Hydrochloric acid TRY (2 mL) was added to the suspension until the mixture was homogeneous. The solution was cooled and kept at 0-5 °C in an ice bath and diazotized by addition of a solution of NaNO, (0.56 g, 8.11 mmol) in water (5 mL) followed by stirring for 0.5 h at 0-5 C. The

Explanation / Answer

For the given azo reaction, homogeneous becomes all the reactant becomes one phase. So bromoaniline would dissolve in water and HCl completely to form single phase reaction mixture. To mix everything well it would be necessary to stir the mixture. Alcohol would not be sufficiently polar for the reaction to occur. With formation of diazo compound which is very reactive, the reaction must be run in an atmosphere of N2 to keep everything stable. Try to cool the reaction mixture not lower than 0-5 oC or reaction would be very slow and may not give the product. Use water-ice mixture and not ice bath for cooling.

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