Synthetic Route of 41175-50-2 , The common heterocyclic compound, 41175-50-2, name is 1,2,3,5,6,7-Hexahydropyrido[3,2,1-ij]quinolin-8-ol, molecular formula is C12H15NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
In a screw-cap bottle, 8-hydroxyjulolidine 10 (0.60 g, 3.17 mmol) and trimellitic anhydride 11 (1.83 g, 9.51 mmol) were suspended in acetic acid (15 mL) and flushed with argon. Cone. H2 S O4 (1 drop) was added, and the reaction mixture was gradually heated in an oil bath (up to 100 C) and stirred for 2.5 h. The precipitate dissolved at about 80-90 C, and a red solution formed. After about 0.5 h, a “new” precipitate was formed. After cooling to room temperature, the purple suspension was transferred into centrifuge test-tubes, sonicated for several seconds in an ultrasonic bath, centrifuged, and the purple supernatant solution was discarded. The precipitate was washed with acetic acid (5 mL) ; the same sonication centrifugation cycles were repeated 5 – 6 times, until the supernatant solution became colorless. The solid residue was dried in vacuo to obtain 0.48 g (40%) of benzophenone 12a with traces of 12b (>95:<5). Beige solid; TLC: ACN/H20/DCM, 9:1:1. HPLC (Eurospher-100 C18 5 pm 250x4 mm, 1.2 mL/min; solvent A: water + 0.1% v/v trifluoroacetic acid (TFA) ; solvent B: MeCN + 0.1% v/v TFA). A/B: 30/70 - 100/0, 25 min, tR = 9.7 min (12a), 10.7 min (12b). NMR (400 MHz, DMSO-d6) delta 12.82 (s, 1H) , 8.09 (0228) (dd, J = 8.1, 1.7 Hz, 1H) , 8.02 (d, J = 8.1 Hz, 1H) , 7.76 (d, J = 1.7 Hz, 1H) , 6.39 (s, 1H) , 3.24 (td, J = 7.4, 4.8 Hz, 4H) , 2.58 (t, J = 6.4 Hz, 2H) , 2.40 (t, J = 6.2 Hz, 2H) , 1.91-1.78 (0229) (m, 2H) , 1.80-1.69 (m, 2H) . C2iHi9N06 (381.12124). MS (ESI): ml z (0230) (negative mode, %) = 380 (100) [M-H]-.
The synthetic route of 41175-50-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E. V.; BUTKEVICH, Alexey; BELOV, Vladimir N.; HELL, Stefan W.; KAMIN, Dirk; SIDENSTEIN, Sven; SHOJAEI, Heydar; KOLMAKOV, Kirill; SOKOLOV, Viktor V.; (116 pag.)WO2018/46753; (2018); A1;,
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