Downstream synthetic route of 7-Nitro-1,2,3,4-tetrahydroisoquinoline

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO84,mainly used in chemical industry, its synthesis route is as follows.,42923-79-5

Combined solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (1.0 g, 5.61 mmol), Boc2O (2 mL, 8.42 mmol) and Et3N (1.5 mL, 11.22 mmol) dissolved in THF (12 mL) was stirred at room temperature for 2 h. After reaction completion, quenched with water, extracted with chloroform (3 X 50 mL). Evaporation of the solvent and purification of the resulting crude by silica gel column chromatography provided the desired product as a colorless viscous oil in 87% yield.1H NMR (400 MHz, Chloroform-d) delta 8.04 – 7.98 (m, 2H), 7.29 (d, J = 8.2 Hz, 1H), 4.66 (s, 2H), 3.69 (t, J = 5.9 Hz, 2H), 2.93 (t, J = 5.9 Hz, 2H), 1.50 (s, 9H). Yield: 87%.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Nitro-1,2,3,4-tetrahydroisoquinoline,belong tetrahydroisoquinoline compound

Reference£º
Patent; SOUTHERN RESEARCH INSTITUTE; OYAGEN, INC.; ANANTHAN, Subramaniam; AUGELLI-SZAFRAN, Corinne E.; BENNETT, Ryan P.; SMITH, Harold C.; VENUKADASULA, Phanindra Krishna Mohan; (227 pag.)WO2019/133666; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem