Someone asked me if I had any patent numbers on making indole from aniline and ethylene glycol after I posted something about it. I told them I was more interested in phenylhydrazones (ie. see US patent 3790596) and didn't copy any numbers down. I got curious later and did a search in 548/469 and 548/508. I started finding some that were issued around 1984 and then did a computer search. Here's a list.
4436916 4436917 4404063 4443615 4456760 4473698 4474969 4476310 4659841 4727161 4732654 4831158 4937353 5175308
There might be more, but I didn't have time to look. Some other patents of interest are:
5037845 DMT derivative
4112231 aniline and epoxides
2748178 toluene + ethylene --> n-propylbenzene
2995566 tryptamine via Fisher synthesis
3953442 IT-290 related compounds
3965182 phenol + amine + aluminum nitride --> anilines
2701251 glutamic acid --NaOCl--> --H+--> CHOCH
2CH
2COOH
make the phenylhydrazone, then Fisher synth to get indole-3-acetic acid
http://www.geocities.com/dritte123/PSPF.html