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.
To a stirring solution of 7-nitro- 1,2,3, 4-tetrahydro-isoquinoline (5.00 g, 23.3 mmol) in dry 1,2-dichloroethane (200 mL) add formalin (37% aq. formaldehyde) (1.91 mL, 25.6 mmol) followed by sodium triacetoxyborohydride (23.4 g, 104.8 mmol). Stir the reaction vigorously at rt for 24 h. TLC (10% MeOH/DCM) indicates formation of desired product (Rf = 0.35) and absence of starting material. Concentrate the reaction in vacuo and dilute the residue with EtOAc (400 mL). Quench this with portionwise addition of sat. NaHCC^ (400 mL) and vigorous stirring (delayed onset of vigorous bubbling). Extract the aqueous with more EtOAc (400 mL), dry the combined organics (Na2S04), and concentrate in vacuo to give a brown oil. Purify the crude product by silica gel chromatography eluting with a gradient of 0% to 2.5% MeOH/DCM to afford an oil. This crystallizes to a solid overnight in vacuo to give the desired product 2-methyl-7-nitro- 1,2,3, 4-tetrahydro- isoquinoline as a solid (3.43 g, 17.3 mmol).
42923-79-5, 42923-79-5 7-Nitro-1,2,3,4-tetrahydroisoquinoline 6424833, atetrahydroisoquinoline compound, is more and more widely used in various fields.
Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; COOK, Brian Nicholas; KOWALSKI, Jennifer A.; LI, Xiang; MARSHALL, Daniel Richard; SCHLYER, Sabine; SIBLEY, Robert; SMITH-KEENAN, Lana Louise; SOLEYMANZADEH, Fariba; SORCEK, Ronald John; YOUNG, Erick Richard Roush; ZHANG, Yunlong; WO2012/6203; (2012); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem