UnintentionalChaos - 24-4-2007 at 21:13
This is a bit out of my range of knowledge (hence me asking), but I am looking to prepare a dye precursor for a dye called rosindone (Doing a google
search turns up something like 11 hits, the most relevant of which are links to our site's library). The compound is 4-nitro,phenylazonaphthalene (No
idea if I named that correctly). The structure is an azo coupling of benzene with naphthalene (attached to the 1 position) with a nitro group on the 4
position of the naphthalene. Can this be done by adding 1-nitronaphthalene to diazotized aniline, or will it want to attach itself in the 3 position
or on the other ring? If this is the case, any ideas on how to get it into the correct arrangement?
matei - 25-4-2007 at 07:34
1-nitronaphthalene won't react with diazotized aniline. Diazonium salts are very weak electrophiles so they only react to give coupling products (i.e.
azoderivatives) with aromatic amines and phenols (and some heterocycles like phenyl-methyl-pyrazolone). I think the only way to go is to diazotize
1-naphthylamine, react it with aniline and get 4-aminophenylazonaphthalene and then make the nitroderivative via a diazonium salt.