Category: 91-21-4

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

91-21-4, Concentrated sulfuric acid (70 mL) was cooled in an ice-salt bath to 00C. 1,2,3,4- Tetrahydroisoquinoline (96percent, 19.6 g, 141 mmol) was added dropwise in portions over 35 minutes, with the temperature mostly staying below 200C, but occasional brief excursions as high as 400C. The resulting mixture was again cooled in an ice-salt bath to 00C and solid potassium nitrate (15.7 g, 155 mmol) was added in portions over 60 minutes, keeping the temperature mostly below 5¡ãC with occasional brief excursions as high as 7¡ãC. Following completion of addition, the bath was removed and the resulting mixture was allowed to stir overnight at ambient temperature. The mixture was added carefully in small portions over 2 hours to concentrated ammonium hydroxide (200 mL), cooled initially in an ice-salt bath to – 2¡ãC. The resulting mixture was diluted with chloroform (400 mL) and the mixture stirred overnight at ambient temperature. Additional concentrated ammonium hydroxide was added to bring the pH to about 11. The mixture was transferred to a separatory funnel and the organic layer was dried over sodium sulfate and evaporated to give about 25 g of dark red oil. This oil was redissolved in ethanol (100 mL), and to the resulting stirred solution was added concentrated hydrochloric acid (10 mL). The mixture immediately formed a hard solid. Additional ethanol (100 mL) and concentrated hydrochloric acid (10 mL) were added, and after stirring for a few minutes, the resulting precipitate was collected by filtration, washed with ethanol, and air-dried. The precipitate was heated to boiling with methanol (200 mL), and the mixture was allowed to cool to ambient temperature and stand overnight. The precipitate was collected by filtration, washed with methanol, and dried under vacuum to afford 7-nitro-l,2,3,4-tetrahydroisoquinoline hydrochloride as an off-white solid (7.05 g, 23percent yield).

As the paragraph descriping shows that 91-21-4 is playing an increasingly important role.

Reference£º
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1: Synthesis of 3′-hydroxy-biphenyl-4-carboxylic acid 3-(2-methyl-l,2,3,4- tetrahydro-isoquinolin-7-ylcarbamoyl)-benzylamide (Compound 1, Table 1); To concentrated H2S04 (100 mL) at 4C add 1,2,3 ,4-tetrahydro-isoquinoline (24.01 g, 180.3 mmol) dropwise keeping the temp below 15C. To the stirring mixture at 4C add NaNC>3 (20.04 g, 198.2 mmol) carefully keeping internal temp below 10 C and stir the mixture overnight at rt. Carefully add the reaction to stirring NH4OH (300 mL) to a final pH = 8. Extract the mixture with DCM (3 x 200 mL) and wash the organic phase with brine (100 mL). Dry the mixture (Na2S04), filter and concentrate. Dissolve the crude residue in EtOH (80 mL) and add concentrated HC1 (25 mL) resulting in a light brown solid which crystallizes in MeOH to give the desired product 7-nitro-l,2,3,4-tetrahydro- isoquinoline (21.91 g, 123.0 mmol)., 91-21-4

Big data shows that 91-21-4 is playing an increasingly important role.

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

91-21-4, 1,2,3,4-Tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

91-21-4, Synthesis of 7-nitro-1,2,3,4-tetrahydroisoquinoline (31-2) 1,2,3,4-Tetrahydroisoquinoline (4.0 g, 30.0 mmol) was dissolved in 10 N of sulfuric acid (6 mL, 30.0 mmol) and then evaporated to dryness to afford a solid residual. This sulfate was added slowly to a solution of potassium nitrate (3.34 g, 33.0 mmol) in sulfuric acid (15 mL), taking care that the temperature of the reaction mixture did not rise above 5 C. After being stirred at room temperature for a further 27 h, the reaction mixture was slowly poured into a con. ammonium solution (ca. 100 mL) under ice cooling. The resulted solution was extracted with dichloromethane (100 mL*3). The combined organic phase was washed with brine (150 mL), dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography (DCM:MeOH=100:1) to afford 31-2 as a brown solid (2.24 g, yield 41%).

As the paragraph descriping shows that 91-21-4 is playing an increasingly important role.

Reference£º
Patent; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91-21-4,1,2,3,4-Tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

A. 7-Nitro-1,2,3,4-tetrahydro-isoquinoline To 43.1 g (324 mmol) of 1,2,3,4-tetrahydro-isoquinoline was added 160 mL of concentrated sulfuric acid with ice bath cooling. Potassium nitrate 35.2 g (348 mmol) was added in portions to the stirring mixture, while maintaining an internal temperature below 5 C. The mixture was allowed to stand at ambient temperature for 72 h, and then basified with aqueous ammonia and extracted four times with chloroform. The combined organics were dried over MgSO4 and concentrated to give a dark brown oil. The oil was dissolved in 240 mL of ethanol and 40 mL of concentrated hydrochloric acid was added to the mixture with cooling. The precipitated material was collected by filtration and washed with cold ethanol to give 25.0 g of a tan solid. The crude material was partitioned between 1 N NaOH and ethyl acetate. The ethyl acetate layer was washed once with brine, dried over Na2 SO4 and concentrated. The dinitrated tetrahydroisoquinoline was removed by crystallization from ether/hexanes. The mother liquor was concentrated to give 2.19 g of 7-Nitro-1,2,3,4-tetrahydro-isoquinoline. B.[{1-[1-(R)-Benzyloxymethyl-2-(7-nitro-3,4-dihydro-1H-isoquinolin-2-yl)-2-oxo-ethylcarbamoyl]-1-methyl-ethyl]-carbamic acid tert-butyl ester According to General Procedure A, 100 mg (0.57 mmol) of 6A and 228 mg (0.60 mmol) of 3 were coupled, and the product was purified by silica gel chromatography (99:1 v/v CH2 Cl2:MeOH) to give 220 mg of 6B as a white foam., 91-21-4

The synthetic route of 91-21-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc; US5936089; (1999); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.91-21-4,1,2,3,4-Tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.,91-21-4

All amines were purchased from Sigma-Aldrich (Merk) except7-nitro-1,2,3,4-tetrahydroisoquinoline 18 and 1-(2,4-dimethylphenyl)-N-methylmethanamine 19, the synthesis ofwhich is summarized below.On an ice bath (0 C), a 100-mL round bottom flask with 1.3 g(10 mmol) of 1,2,3,4-tetrahydroquinoline and 5mL of conc. H2SO4was allowed to stir for 10 min. To this solution, 1.1 g (10 mmol) ofKNO3 were added in small portions, taking care that the temperatureof the reaction did not rise above 5 C. The reactionwas stirredovernight and monitored by TLC (DCM/EtOH 90:10). The brownsolution was neutralized with a solution of diluted NH4OH untilpH 8 and the basic mixture was extracted with DCM (3 x 50 mL).The combined organic extracts were washed with brine (once),dried and filtered. The evaporation of the solvent affords a red oilwhich was dissolved in the minimum amount of abs. EtOH andcooled on an ice bath. The alcoholic solution was treated with2.5 mL of conc. HCl to affords a yellow precipitate of 7-nitro-1,2,3,4-tetrahydroisoquinoline 18, which was recrystallized from MeOH.Yellow solid; m.p.: 261-263 (260-262 C [57]); Yield: 32%; I.R.(nujol, cm-1): 3173; 1H NMR (CDCl3-TMS) delta: 1.86 (br s, 1H, NHdisapp. on D2O), 3.12 (t, 2H, H-4, J 8 Hz), 3.46 (t, 2H, H-3, J 8 Hz),4.37 (s, 2H, H-1), 7.36 (d, 1H, arom. H-5, J 12 Hz), 8.00 (m, 2H,arom. H-6 and H-8).

As the paragraph descriping shows that 91-21-4 is playing an increasingly important role.

Reference£º
Article; Zampieri, Daniele; Fortuna, Sara; Calabretti, Antonella; Romano, Maurizio; Menegazzi, Renzo; Schepmann, Dirk; Wuensch, Bernhard; Collina, Simona; Zanon, Davide; Mamolo, Maria Grazia; European Journal of Medicinal Chemistry; vol. 180; (2019); p. 268 – 282;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem