WangleSpong5000 - 20-4-2018 at 17:33
So the action of nitrous acid/diazonium ion(s) on the lone OH group on the 2 position on the benzene ring can be made into an amino group just as the
inverse can be done, but what protects the carbonyl group OH? Is it something to do with the nitrous acid not reacting with this OH group as the
double bond on the Oxygen is a kind of resonating structure as part of the carbonyl group and as a result of this the diazonium ion can't be made via
the nitrous acid?
Maybe not a resonance structure but the polar equivalent I can't remember the name of?
Chemi Pharma - 20-4-2018 at 22:22
If you want to convert salicylic acid into anthranilic acid directly, in one pot, follow the direction given by the paper below about conversions of
phenols into amines with chloroacetamide, K2CO3, KI, DMF system:
Attachment: phenols to anilines with chloroacetamide, K2CO3, KI and DMF.PDF (1.9MB)
This file has been downloaded 546 times
byko3y - 21-4-2018 at 18:35
WangleSpong5000, I don't understand what you mean by "action of nitrous acid/diazonium ion(s) on the lone OH group on the 2 position
on the benzene ring can be made into an amino group". Second position relative to what? To NH2 group? Then the ring already contains amino group - why
do you need to introduce it?
Benzenediazonium carboxylates are existing compounds, probably unstable though. Carboxylic group requires a lot of energy to be broken.
LearnedAmateur - 22-4-2018 at 02:00
Nitrous acid reacts with OH groups to form nitrite esters, which are good protecting groups, but don’t form amines. Nitrous acid reacts with amines
to form diazonium salts, which are not useful at all in this case since the nitrogen will leave the reaction as N2, the Sandmeyer reaction. So, it’s
easy to make salicylic acid from anthranilic acid via that method (reaction with H2O to replace -NH2 with -OH) but I don’t think nitrous acid would
be overly useful for the other way around.
[Edited on 22-4-2018 by LearnedAmateur]