How to convert NO2 group into Carboxylic acid for macrocyclic compounds ?

I synthesized the pyrimidine carboxylic acid in acetic acid as solvent and catalyst but after putting the reaction mixture into ice it does not solidify then I used the solvent extraction with ethyl acetate to separate my product. I removed all the water but still even at rotary evaporator it still not solidify due to trapping of acetic acid. I tried solvent extraction again and again but did not work.

It always need to functionalize a secondary alcohol with leaving group (e.g. OTf, OMs), nucleophilic substitution of the leaving group to afford an OH with configuration inversions , and then functionalizing the OH again and substituted with NaN₃ (or Mitsunobu reaction, e.g. DPPA) .

Another method is oxidation of the secondary alcohol and then reduction the ketone to afford OH with a pair of enantiomer, and then do same things again.

Is there any efficient method to directly turn a secondary alcohol into the azide and keep configuration retention?

Or any efficient method to directly Azidation and to avoid the elimination reaction?

There is a Michael acceptor in one substrate that could potentially react with amine in the second substrate, how can I block this reaction? is there any blocking group for Michael acceptor.

How to write Spectroscopic Notations for organic molecules?

I synthesized schiff base from P-anisidine and n,n-dimethylaminobenzaldehyde. But my p-anisidine is not pure. So I want to recrystalize it. So for DNP also. DNP used for another schiff base with vanillin. Thank you

description is in the file attached.

I have tried Cu/CuI as well as the palladium catalyzed reaction but it seem not to work.

Hello ! I'm designing a scaffold-structure in which at one point I have an ethyl ester, a substituted amide ( with different kind of substituents, thiazolyl, alkyl C-terminal halides, phenyl, naphthalene, pyridine etc.) and a cyclic amine acylated with Boc anhydride. I'm thinking, if I really really need to deprotect that cyclic amine would this affect and destroy the ethyl ester and the other amide? I'm thinking TFA would be a well known reagent for deprotection of an amine acylated by boc anhydride. Is this feasible? I know that probably the answer to everything related to why and how and to be or not to be, like always is, try it, and you'll see but I really wanted to see your perspective on this topic, I really,strongly doubt it that nobody has ever dealt with this kind of situation.

Thank you!