This paper claims to use dil HNO3/AcOH to selectively nitrate salicylic acid (amongst others) to give ONLY 5-nitrosalicylic acid

Reaction with HNO3/HOAc

By the addition of concentrated HNO3 to glacial HOAc, dilute HNO3 (about 15% concentration) was prepared and used for the nitration of salicylaldehyde and salicylic acid. The progress of reaction was monitored by TLC. It was observed that the microwave assisted reaction for a nitric acid/acetic acid mixture was very fast. In case of salicylaldehyde the same product (4) was obtained that was produced by reaction with aqueous HNO3. In the case of salicylic acid, the product obtained - in high yield and good purity - was the 5-nitro isomer. This reaction again was very fast - almost
5-10 times faster than the reaction with aqueous HNO3.

Given that I have requested another paper on the use of phenylhydrazones - in this case maybe from the 5-nitrosalicylic acid to the aniline via reduction, then to the phenylhydrazine, reaction via the glutamic acid paper I'm requesting to give the 4-carboxy-5-hydroxy-indoleacetic acid (maybe even 4,5-dihydroxy/4,5-dimethoxy/4,5-methylenedioxy-DMT might become accessible).

Think about that a minute - 4-hydroxyDMT is Psylocin & 5-hydroxyDMT is Bufotenin, so the potential is there, not to mention that a-methyldopamine with two hydroxy groups (ie. 3,4-dihydroxyamphetamine) shows dramatically different pharmacology when N-methylated and when either two methoxy groups (DMA & DMMA) or a methylenedioxy group (MDA & MDMA) are attached to those 3,4-hdyroxyl's...In fact, 5-MeO-DMT is already known to be active, but I don't think either Hoffman or Shulgin even tried 4-MeO-DMT, let alone 4,5-MD-DMT.

See why I wanted a NOVEL topic?