Category: 91-21-4

Name is 1,2,3,4-Tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 91-21-4, its synthesis route is as follows.,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).

With the complex challenges of chemical substances, we look forward to future research findings about 1,2,3,4-Tetrahydroisoquinoline

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

As a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, name is 1,2,3,4-Tetrahydroisoquinoline, and cas is 91-21-4, its synthesis route is as follows.,91-21-4

Reference Example 29 7-Amino-3,4-dihvdro-l//-isoquinoIine-2-carboxylic acid benzyl ester; 1,2,3,4-Tetrahydroisoquinoline (10 ml; 80 mmol) was added dropwise over 10 min. to stirred cone. H2SO4 at 0 ¡ãC. KNO3 was added portionwise over 5 min. at 0 ¡ãC and the resulting mixture was stirred overnight whilst allowing to warm to r.t. The reaction mixture was quenched by pouring onto iced water (300 ml) and basified with NH4OH. The mixture was extracted with CH2Cl2 (2 * 300 ml), the combined organic layers were dried (Na2SO4) and concentrated. The dark red residue was dissolved in EtOH (400 ml) and treated with HCl(g) for 5 min. The resulting solid was recrystallised from EtOH to give 7-nitro-l,2,3,4- tetrahydro-isoquinoline hydrochloride as an off-white solid (4.69 g).

With the complex challenges of chemical substances, we look forward to future research findings about 91-21-4,belong tetrahydroisoquinoline compound

Reference£º
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125839; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4,the tetrahydroisoquinoline compound, it is a common compound, a new synthetic route is introduced below.

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).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1,2,3,4-Tetrahydroisoquinoline, 91-21-4

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

1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

91-21-4, To ice cold concentrated sulfuric acid was added in a dropwise manner 1,2, 3,4- tetrahydroisoquinoline (23 mL, 170 MMOL), followed by potassium nitrate (18.8 g, 186 mmol) at such a rate that the temperature did not rise above 5 C. After complete addition the mixture was stirred at room temperature for 18 h then poured onto a stirred mixture of ice (700 g) and NH40H (150 ML). The mixture was extracted with CHC13 (3 x 300 mL). The combined CHCl3 layers were washed with saturated NaCl (200 ML), dried over NA2SO4, filtered and concentrated in vacuo. The residue was dissolved in ethanol (130 mL) and cooled in an ice bath as concentrated hydrochloric acid (22 mL) was added. The formed precipitate was removed by filtration and recrystallized from methanol to give the product (12.45 g, 34 %) ; H NMR 500MHZ (DMSO-d6) No. = 3,. 13 (2H, t, J = 6. 2 Hz), 3.35 (2H, t, J = 6. 2 Hz), 4.35 (2H, s), 7.50 (LH, d, J=8. 5HZ), 8.07 (1H, dd, J=2. 3and8. 5Hz), 8.19 (1H, d, J=2. 3Hz) 10.02 (2H, br S).

As the rapid development of chemical substances, we look forward to future research findings about 91-21-4

Reference£º
Patent; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2004/94371; (2004); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

91-21-4,1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

In a mortar 2 g of P2O5/silica gel (65% w/w)1 (10 mmol) and 1,2,3,4-tetrahydroisoquinoline (10 mmol, 1.33 g) was triturated for 30 s, and then 5 ml of HNO3 65% was added drop-wise and the mixture was further triturated with a pestle at room temperature for 20 min until a deep-yellow color appeared, at which point TLC (n-hexane:EtOAc 70:30) showed complete disappearance of 1,2,3,4-tetrahydroisoquinoline (30 min). To the reaction mixture was added diethyl ether (50 ml) and the solid was separated through a short pad of silica gel and washed with diethyl ether (2 ¡Á 15 ml). The filtrate was washed with NaHCO3 10% (20 ml) and dried (MgSO4). The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (n-Hexane:EtOAc, 2:1), 7-nitro-1,2,3,4-tetrahydroisoquinoline (2b) was obtained (8 mmol, 1.4 g 80%) as a yellow solid, mp 121 C. 1H NMR, delta: 8.05 (m, 2H), 7.60 (m, 1H,), 3.82 (s, 2H), 3.38 (t, 2H, J = 7.4 Hz), 3.12 (t, 2H, J = 7.4 Hz), 2.83 (s, 1H). 13C NMR, delta: 150.6, 145.0, 140.3, 129.6, 122.6, 121.4, 46.9, 44.1, 28.1. EMS [M+H+] for C9H10N2O2, Calcd 179.0740. Found, 179.1121.

91-21-4 is used more and more widely, we look forward to future research findings about 1,2,3,4-Tetrahydroisoquinoline

Reference£º
Article; Hajipour, Abdol R.; Guo, Lian-Wang; Pal, Arindam; Mavlyutov, Timur; Ruoho, Arnold E.; Bioorganic and Medicinal Chemistry; vol. 19; 24; (2011); p. 7435 – 7440;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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

Reference Example 29 7-Amino-3,4-dihvdro-l//-isoquinoIine-2-carboxylic acid benzyl ester; 1,2,3,4-Tetrahydroisoquinoline (10 ml; 80 mmol) was added dropwise over 10 min. to stirred cone. H2SO4 at 0 ¡ãC. KNO3 was added portionwise over 5 min. at 0 ¡ãC and the resulting mixture was stirred overnight whilst allowing to warm to r.t. The reaction mixture was quenched by pouring onto iced water (300 ml) and basified with NH4OH. The mixture was extracted with CH2Cl2 (2 * 300 ml), the combined organic layers were dried (Na2SO4) and concentrated. The dark red residue was dissolved in EtOH (400 ml) and treated with HCl(g) for 5 min. The resulting solid was recrystallised from EtOH to give 7-nitro-l,2,3,4- tetrahydro-isoquinoline hydrochloride as an off-white solid (4.69 g).

91-21-4,1,2,3,4-Tetrahydroisoquinolinebelongs to tetrahydroisoquinoline compound, is more and more widely used in various fields. and we look forward to future research findings.

Reference£º
Patent; PIRAMED LIMITED; THE INSTITUTE OF CANCER RESEARCH; WO2008/125839; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

91-21-4, To concentrated H2504 solution (62 mL) at 4 C was added 1,2,3,4- tetrahydroisoquinoline (15 g, 112.78 mmol) dropwise keeping the temperature below 15 C. To the stifling mixture at 4 C was added NaNO3 (12.5, 148.80 mmol) keeping internal temperature below 10 C. The reaction mixture was stined at RT for 16 h. The reaction mixture was added to NH4OH (185 mL) to a final pH = 8. The mixture was extracted with DCM (3 x 150 mL), washed with brine (75 mL) and dried (Na2504). The solvent was removed. The resulting crude was dissolved in EtOH (50 mL) and concentrated HC1 (14 mL) was added. The resulting solid was filtered and washed with diethyl ether to afford 7-nitro- 1,2,3,4-tetrahydroisoquinoline (13 g, 86%) as a mixture of isomers. MS (ESI) mlz: 179.1 [M+H].

As the rapid development of chemical substances, we look forward to future research findings about 91-21-4

Reference£º
Patent; ZENO ROYALTIES & MILESTONES, LLC; HUANG, Peter, Qinhua; BOREN, Brant, Clayton; BUNKER, Kevin, Duane; LIU, Hui; PALIWAL, Sunil; (99 pag.)WO2019/28008; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1,2,3,4-Tetrahydroisoquinoline, cas is 91-21-4, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

91-21-4, 1,2,3,4-Tetrahydroisoquinoline (6.3 mL, 50.0 mmol) was added dropwise to a stirred ice-cold solution of concentrated H2SO4 (25 mL). KNO3 (5.6 g, 55.0 mmol) was added portionwise while maintaining the temperature below 5¡ã C. The mixture was stirred at room temperature overnight, carefully poured into an ice-cold solution of concentrated NH4OH, and then extracted three times with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting dark brown oil was taken up into EtOH, cooled in an ice bath and treated with concentrated HCl. The yellow precipitate was collected via filtration and recrystallized from methanol to give 1,2,3,4-tetrahydro-7-nitroisoquinoline hydrochloride as yellow solid (2.5 g, 23percent). 1H NMR (400 MHz, DMSO-d6) delta 9.86 (s, 2H), 8.22 (d, J=1.6 Hz, 1H), 8.11 (dd, J=8.5, 2.2 Hz, 1H), 7.53 (d, J=8.5 Hz, 1H), 4.38 (s, 2H), 3.38 (s, 2H), 3.17-3.14 (m, 2H); HPLC ret. time 0.51 min, 10-99percent CH3CN, 5 min run; ESI-MS 179.0 m/z (MH+).

As the rapid development of chemical substances, we look forward to future research findings about 91-21-4

Reference£º
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Name is 1,2,3,4-Tetrahydroisoquinoline, as a common heterocyclic compound, it belongs to tetrahydroisoquinoline compound, and cas is 91-21-4, its synthesis route is as follows.,91-21-4

EXAMPLE 110; Step A; To ice cold concentrated sulfuric acid was added in a dropwise manner 1,2,3,4-tetrahydroisoquinoline (23 mL, 170 mmol), followed by potassium nitrate (18.8 g, 186 mmol) at such a rate that the temperature did not rise above 5 C. After complete addition the mixture was stirred at room temperature for 18 h then poured onto a stirred mixture of ice (700 g) and NH4OH (150 mL). The mixture was extracted with CHCl3 (3¡Á300 mL). The combined CHCl3 layers were washed with saturated NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was dissolved in ethanol (130 mL) and cooled in an ice bath as concentrated hydrochloric acid (22 mL) was added. The formed precipitate was removed by filtration and recrystallized from methanol to give the product (12.45 g, 34%); 1H NMR 500 MHz (DMSO-d6) delta=3.13 (2H, t, J=6.2 Hz), 3.35 (2H, t, J=6.2 Hz), 4.35 (2H, s), 7.50 (1H, d, J=8.5 Hz), 8.07 (1H, dd, J=2.3 and 8.5 Hz), 8.19 (1H, d, J=2.3 Hz) 10.02 (2H, br s).

With the complex challenges of chemical substances, we look forward to future research findings about 1,2,3,4-Tetrahydroisoquinoline

Reference£º
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); A1;,
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.

1,2,3,4-Tetrahydroisoquinoline (6.3 mL, 50.0 mmol) was added dropwise to a stirred ice-cold solution of concentrated H2SO4 (25 mL). KNO3 (5.6 g, 55.0 mmol) was added portionwise while maintaining the temperature below 5¡ã C. The mixture was stirred at room temperature overnight, carefully poured into an ice-cold solution of concentrated NH4OH, and then extracted three times with CHCl3. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting dark brown oil was taken up into EtOH, cooled in an ice bath and treated with concentrated HCl. The yellow precipitate was collected via filtration and recrystallized from methanol to give 1,2,3,4-tetrahydro-7-nitroisoquinoline hydrochloride as yellow solid (2.5 g, 23percent). 1H NMR (400 MHz, DMSO-d6) delta 9.86 (s, 2H), 8.22 (d, J=1.6 Hz, 1H), 8.11 (dd, J=8.5, 2.2 Hz, 1H), 7.53 (d, J=8.5 Hz, 1H), 4.38 (s, 2H), 3.38 (s, 2H), 3.17-3.14 (m, 2H); HPLC ret. time 0.51 min, 10-99percent CH3CN, 5 min run; ESI-MS 179.0 m/z (MH+)., 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; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem