Pelchowicz, Zvi published the artcileSubstituted tryptamines and their derivatives, HPLC of Formula: 102236-19-1, the publication is Journal of the Chemical Society (1960), 4699-701, database is CAplus.
o-MeC6H4NH2 (21.3 g.), 54 ml. concentrated HCl, and 236 ml. H2O diazotized with 15 g. NaNO2, 10% aqueous Na2CO3 added at 0° to bring the pH to 5-6, the whole filtered, added to 34 g. Et 2-oxopiperidine-3-carboxylate (I), 400 ml. H2O, and 12 g. KOH (kept 24 hrs. at room temperature before use), the pH adjusted to 34 with AcOH, and the whole kept 48 hrs. at 0° gave 35 g. 3-(o-tolyl)hydrazone of 2,3-dioxopiperidine (II), m. 140.0-40.5° (aqueous alc.). 3-(p-Tolyl)hydrazone of 2,3-dioxopiperidine (III) was similarly obtained, 81%, m. 209-9.5°. Crude II (45 g.), 200 ml. AcOH, and 100 ml. concentrated HCl refluxed 1 hr., cooled, and diluted with H2O gave 28.8 g. 1,2,3,4-tetrahydro-8-methyl-1-oxo-β-carboline (IV), m. 228.5-29° (aqueous alc.); III similarly gave 83% 6-Me analog of IV, m. 187.5-8.5° (aqueous alc.). III (28 g.), 260 ml. alc., and 260 ml. 4N aqueous KOH refluxed 1 hr., concentrated to half volume, diluted with 250 ml. H2O, and neutralized with AcOH gave 24 g. 7-methyltryptamine-2-carboxylic acid (V), m. 278-81°; the 5-Me analog (VI) of V was obtained similarly, 83%, m. 267-7.5° (decomposition). V (10.5 g.) and 400 ml. 5% HCl refluxed until CO2 evolution ceased, the whole cooled, and neutralized with NaOH gave 7.2 g. 7-methyltryptamine (VII), purified by sublimation, m. 130-1°; 5-methyltryptamine, obtained in 76% yield from VI, m. 99-9.5° (Et2O-petr. ether). Diazotized 5,2-FMeC6H3NH2 and I as above gave 72% 5-F derivative (VIII) of II, m. 204.5-5.0°, and VIII was used as above to obtain 73% 5-F derivative of IV, m. 204.5-5.0° (aqueous alc.), 80% 4-F derivative of V, m. 273° (decomposition) (H2O), and 4-F derivative of VII, m. 141-2° (after sublimation). VIII (5 g.), 100 ml. 10% aqueous AcH, 16 ml. 2N H2SO4, and 100 ml. H2O heated 0.33 hr. at 110°, cooled, and treated with excess alkali gave 4.9 g. 6-fluoro-1,2,3,4-tetrahydroharmaline, m. 201-2° (by sublimation) (L.D.50 600 mg./kg. in mice). VIII (5.74 g.), 1 g. NaHCO3, and 25 ml. Ac2O refluxed 0.25 hr., poured into H2O, the whole treated with excess Na2CO3, and extracted with Et2O gave 5.5 g. Nα-Ac derivative (IX), m. 127.5-8.0° (Et2O-petr. ether). To 5 g. IX in 200 ml. hot xylene was added in small portions 50 g. P2O5; the whole refluxed 2 hrs., the solid filtered off and added in small portions to 500 ml. 5% HCl, the whole heated at 80°, filtered, the filtrate cooled, treated with excess alkali and extracted with Et2O gave 6-fluoro-3,4-dihydroharmaline, m. 206-7° (aqueous alc.).
Journal of the Chemical Society published new progress about 102236-19-1. 102236-19-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Chloride, name is 5-(tert-Butyl)-2-chloropyridine, and the molecular formula is C9H12ClN, HPLC of Formula: 102236-19-1.
Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem