Here is an article in Green Chemistry that is exactly what you are looking for. I've also attached a picture so that the numbering scheme is clearer.

Here is the procedure from the paper below:

General procedure for the preparation of azo pigments

For products 1–6, a mixture of the coupling component (1 g), aromatic primary amine (1.05 equiv.), HCl (2 equiv.), H2O (3 mL), NaNO2 (1.10 equiv., in 2 mL of H2O) and granular PTFE (2.5 g) was mechanically stirred (400 rpm) at rt. Thin-layer chromatography (TLC) indicated the completion of the reaction. After stopping the reaction, the products were suspended in water while the granular PTFE precipitated at the bottom of the flask. The suspended products were filtered, washed with water (2 mL) and dried to give a quantitative yield of the product without further purification.

For products 7–25, a mixture of aromatic primary amine (1.05 equiv.), HCl (3 equiv.), H2O (3 mL), NaNO2 (1.10 equiv., in 2 mL of H2O) and granular PTFE (2.5 g) was mechanically stirred (400 rpm) at rt. After 20 min, the coupling component (1 g) was added. The reaction was continued until TLC indicated the completion of the reaction. After stopping the reaction, the products were suspended in water while the granular PTFE precipitated at the bottom of the flask. The suspended products were filtered, washed with water (2 mL) and dried to give a quantitative yield of the product without further purification.

https://pubs.rsc.org/en/content/articlelanding/2019/gc/c8gc03982h#!divAbstract

https://pubs.rsc.org/en/content/articlehtml/2019/gc/c8gc03982h

Thankyou Dear Grant Simpson For Sharing This Valuable Information.

I am sure this will be helpful.

Thankyou Dear Grant Simpson For Sharing This Valuable Information.

I am sure this will be helpful.