7-Nitro-1,2,3,4-tetrahydroisoquinoline, cas is 42923-79-5, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.
7-nitro-1,2,3,4-tetrahydroisoquinoline (1 g, 5.61 mmol), N-Iodosuccinimide (1.64 g, 7.3 mmol) dissolved in Trifluoromethanesulfonic acid (5.5 mL, 61.73 mmol) allowed to react at room temperature overnight. After reaction completion crude reaction mixture was carefully transferred onto sat. NaHCO3 (aq) solution. After complete addition the aqueous layer was extracted with methylene chloride (2 X 75 mL). The combined organic extracts were then washed with aq. Sodium Thiosulfate (sat), dried over Na2SO4 (anhyd) and concentrated under reduced pressure to obtain providing 1.6 g of the crude as a purple color solid in 94% yield. This crude was then carried through next step without purification. 1H NMR (400 MHz, DMSO-d6) delta 8.40 (d, J = 2.4 Hz, 1H), 7.99 (d, J = 2.4 Hz, 1H), 3.88 (s, 2H), 2.96 (t, J = 6.0 Hz, 2H), 2.56 (t, J = 6.0 Hz, 2H). LRMS: (M+H)+ = 305.0 m/z. Yield: 94%.
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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