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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.42923-79-5,7-Nitro-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

2-Methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (252). Formic acid (9.4 mL, 250 mmol) was added dropwise to Ac2O (19 mL, 202 mmol) at 0 0C. The solution was stirred at 50 0C for 45 min, then cooled to -18 0C, diluted with THF (100 mL) and a solution of 7-nitro- 1 ,2,3,4-tetrahydroisoquinoline [(a) Tercel, M.; et al., J. Med. Chem. 1996, 39, 1084-1094; (b) Zhu, Z., et al., J. Med. Chem. 2003, 46, 831-837] (251) (13.8 g, 5.0 mmol) in THF (100 mL) was added and stirred at -15 to -18 0C for 30 min. The solution was warmed to 20 0C, the solvent evaporated and the residue partitioned between saturated aqueous NaHCO3 solution (250 mL) and EtOAc (250 mL). The aqueous fraction was extracted with EtOAc (3 x 250 mL), dried and the solvent evaporated. The residue was dissolved in THF (200 mL), EPO cooled to 10 0C and BH3 DMS solution (10 M, 19.4 mL, 194 mmol) was added. The solution was stirred at 20 0C for 1 h, diluted with MeOH (30 mL) and acidified with HCI solution (1 M, 45 mL). The solution was stirred at 40 0C for 15 min, the solvent evaporated and the residue partitioned between saturated aqueous NaHCO3 solution (250 mL) and EtOAc (250 mL). The aqueous fraction was extracted with EtOAc (3 x 250 mL), dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (2-5%) of MeOH/DCM, to give isoquinoline 252 (12.6 g, 85%) as an orange solid: 1H NMR delta 8.09 (dd, J = 8.4, 2.3 Hz, 1 H, H-6), 7.95 (d, J = 2.3 Hz, 1 H, H-8), 7.37 (d, J = 8.4 Hz, 1 H, H-5), 4.27 (d, J = 16.1 Hz1 1 H, H-1), 3.94 (d, J = 16.1 Hz, 1 H, H-1), 3.23-3.34 (m, 2 H, CH2), 2.99-3.18 (m, 2 H, CH2), 2.17 (s, 3 H, NCH3); MS (APCI) m/z 193 (MH+, 100%).

42923-79-5 7-Nitro-1,2,3,4-tetrahydroisoquinoline 6424833, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; AUCKLAND UNISERVICES LIMITED; WO2006/104406; (2006); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem