Month: August 2020

42923-79-5, 7-Nitro-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stined solution of 7-nitro-2 ,3-dihydro- 1 H-spiro[cyclopropane- 1,4- isoquinoline] (500 mg, 2.45 mmol) in DMF (5 mL) was added K2C03 (1.55 g, 11.23 mmol) at 0 C. After 5 mins, methanesulfonyl chloride (0.4 mL, 5.62 mmol) was added at 0 C, and the reaction was stined at RT for 3 h. The reaction was diluted with water and extracted with EA (2 x 30 mL). The combined organic layers were washed with water (15 mL), dried (Na2SO4), and concentrated. The crude was triturated with pentane to afford 2- (methylsulfonyl)-7-nitro-1,2,3,4-tetrahydroisoquinoline (505 mg, 70%) as a pale yellow solid. MS (ESI) mlz 257.3 [M+H].

As the paragraph descriping shows that 42923-79-5 is playing an increasingly important role.

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

6-Methoxy-1,2,3,4-tetrahydroisoquinoline, cas is 42923-77-3, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

6-Methoxy-l,2,3,4-tetrahydroisoquinoline (14.7 g, 90 mmol) is dissolved into hydrobromic acid (48%, 300 ml), and the mixture is heated at 120 0C for 16 hr. The solvent is removed under reduced pressure to give the title compound as the hydrobromate.

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Reference£º
Patent; NEUROGEN CORPORATION; WO2007/106349; (2007); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-Methoxy-1,2,3,4-tetrahydroisoquinoline, cas is 42923-77-3, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

General procedure: To a stirred solution of 1,2,3,4-THIQ (1.0 equiv.) in CH2Cl2 (10.0 mL/mmol), triethylamine(1.2 equivalent) was added and then cooled to 0 C. Acyl chloride (1.2 equivalent), sulfonyl chloride(1.2 equivalent), or diethylcarbamoyl chloride (1.2 equivalent) was added slowly at 0 C. The resultingreaction mixture was stirred at room temperature for 2 h under an argon atmosphere and thenpoured onto water (10.0 mL/mmol) and the organic layer was separated. The aqueous layer wasextracted two times with CH2Cl2 (10.0 mL/mmol), and the combined organic layer was washed withbrine (5.0 mL/mmol), dried over sodium sulfate, filtered, and concentrated under reduced pressure.Purification of the crude residue by flash column chromatography on silica gel, using the appropriatemixture of eluents, provided the corresponding N-protected 1,2,3,4-tetrahydroisoquinoline. Spectral data(1H- and 13C-NMR) of compounds (5a, 5c, 5d, 5e, 5g, 5h, 5k, 5l, 5m, 5n, 5o, 5q, 5r) which were reportedpreviously were compared and found in agreement with literature data. Furthermore, references wererepresented in supporting information. The characterization of novel compounds is given.

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Reference£º
Article; Kim, Hong Pyo; Yu, Heesun; Kim, Hyoungsu; Kim, Seok-Ho; Lee, Dongjoo; Molecules; vol. 23; 12; (2018);,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, cas is 170097-67-3, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

Intermediate 25: 1 ,1-Dimethylethyl 6-[(1 /-/-pyrazol-4-ylamino)carbonyl1-3,4-dihydro- 2(1 HVisoalphauinolinecarboxylate; To a solution of 1 H-pyrazol-4-amine (1.87 g, 22.5 mmol), N-(3-dimethylaminopropyl)- N’-ethylcarbodiimide hydrochloride (5.18 g, 27 mmol), 1-hydroxybenzotriazole hydrate (3.65 g, 27 mmol) and triethylamine (6.3 ml_, 45 mmol) in DMF was added 2- {[(I J-dimethylethyOoxylcarbonylJ-i ^^^-tetrahydro-theta-isoquinolinecarboxylic acid (5.62 g, 20.3 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The volatiles were removed under reduced pressure, the residue was dissolved in MeOH and potassium hydroxide (5.04 g, 90 mmol), water (100 ml.) was added and the mixture was heated at 500C for 15 min. The MeOH was evaporated under reduced pressure and the solid which crystallized was filtered and recrystallized from acetonitrile to give the title compound as a solid (3.7 g, 48%). LC/MS: m/z 341 (M-H)+, Rt: 2.80 min.

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Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/74824; (2008); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

1-Phenyl-1,2,3,4-tetrahydroisoquinoline, cas is 22990-19-8, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

EXAMPLE 14 STR20 2-(2-chloropropionyl)-1-phenyl-1,2,3,4-tetrahydroisoquinoline By procedures described in Example 1 (Method A), phenethylamine and benzoyl chloride were converted to 1-phenyl-1,2,3,4-tetrahydroisoquinoline. A reaction vessel was charged with 3.0 g of this isoquinoline compound, 5 ml 10% sodium hydroxide and 50 ml methylene chloride. With this mixture stirred, 1 ml 2-chloropropionyl chloride was added dropwise to the mixture. The mixture was stirred for 10 minutes, then water was added. The organic extract was dried with magnesium sulfate, stripped of solvent and subjected to Kugelrohr distillation (170 C. a 0.1 mm Hg) to provide 2.3 g of a viscous yellow oil product having the elemental analysis reported in Table I.

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Reference£º
Patent; Monsanto Company; US4755218; (1988); A;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

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.

To a stined solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline (5 g, 28.09 mmol) in DMF (20 mL) was added K2C03 (15.5 g, 112.36 mmol) followed by ethyl iodide (4.4 mL, 56.18 mmol). The reaction was stined at RT for 3 h. Water (50 mL) was added, and the mixture was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (25 mL), dried (Na2SO4) and concentrated in vacuo. The resulting crude residue was purified by column chromatography (Si02, 30% EA/pet. ether) to afford 2- ethyl-7-nitro-1,2,3,4-tetrahydroisoquinoline (3.1 g, 54%) as a pale yellow liquid. MS (ESI) mlz 207.1 [M+H].

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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

6-Bromo-1,2,3,4-tetrahydroisoquinoline, cas is 226942-29-6, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

To a solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (0.700 g, 3.30 mmol) in DCM (30 mL) was added Intermediate 1-13 (0.640 g, 3.63 mmol) followed by sodium triacetoxyborohydride (1.40 g, 6.60 mmol). The resulting reaction mixture was stirred at ambient temperature for 14 h. The reaction mixture was diluted by water (50 mL) and extracted with DCM (2 x 50 mL). The combined extracts were washed with brine (50mL), dried over anhydrous sodium sulfate and concentrated. The crude was washed withdiethyl ether (2 x 50 mL) to afford Intermediate 6A (1.05 g, 73.5 %) as a brown solid. ?HNIVIR (400 MHz, DMSO-d6) ppm 2.70-2.80 (m, 6 H), 2.99 (t, J= 10 Hz, 2 H), 3.59 (s, 2H), 5.37 (s, 2 H), 7.03 (d, J= 10.8 Hz, 1 H), 7.27 (d, J= 2.4 Hz, 1 H), 7.31 (s, 1 H), 7.50(d, J= 10.4 Hz, 1 H), 7.56 (s, 1 H), 7.76 (d, J= 10.4 Hz, 1 H). LCMS (MethodR):retention time 1.03 mi (M+H) 374.2.

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Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUNAGA, Prashantha; RICHTER, Jeremy; YADAV, Navnath Dnyanoba; PANDA, Manoranjan; GODESI, Sreenivasulu; (132 pag.)WO2017/184662; (2017); 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

1,2,3,4-tetrahydroisoquinolin (10. Og, 75.1mmol, 1 equiv) was dissolved in 40ml of concentrated sulfuric acid (exothermic reaction) and potassium nitrate (8.4g, 83.0mmol,1.1 equiv) was added in portions over lhour whilst stirring at O0C. The reaction mixture was then warmed up to room temperature and stirred for 2hrs. The reaction was poured in ice-water (100ml) and basified to pH 10 with ammonia solution (100ml). The mixture was then extracted with chloroform (2 x 250ml). The combined extracts were washed with brine, dried over magnesium sulfate and concentrated to give a dark red oil. The residue was purified by column chromatography using DCM/MeOH/NH4OH:95/5/0.5 to give the title mixture of isomers as a solid (7g, 52%).1H NMR (CDCl3, 400MHz) delta= 7.99 (m, IH), 7.92 (s, IH), 7.28 (m, IH), 7.26 (m, IH), 4.1 (s, 2H), 3.17 (m, 2H), 2.9 (m, 2H).

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Reference£º
Patent; CELLZOME AG; WO2009/62658; (2009); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-Methoxy-1,2,3,4-tetrahydroisoquinoline, cas is 42923-77-3, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

6.1.19 1,2,3,4-Tetrahydroisoquinolin-6-ol hydrochloride (36) To a solution of 35 (205 mg, 1.26 mmol) in dry dichloromethane (10 mL) was added 1 N BBr3 in dichloromethane (2.6 mL, 2.6 mmol) at -78 C under N2. The mixture was stirred at -78 C for 1 h, and then stirred at room temperature overnight. Methanol (10 mL) was added. The reaction mixture was concentrated under reduced pressure, diluted with 1 N HCl (30 mL) and washed with ethyl acetate (30 mL * 3). The aqueous layer was concentrated to give crude 36 (288 mg) as a yellow solid. 1H NMR (400 MHz, D2O): delta 5.53-5.49 (m, 1H), 5.23-5.14 (m, 2H), 2.69 (d, J = 9.6 Hz, 2H), 1.92-1.84 (m, 2H), 1.50-1.46 (m, 2H).

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Reference£º
Article; Dong, Yan; Li, Kehuang; Xu, Zhixiang; Ma, Haikuo; Zheng, Jiyue; Hu, Zhilin; He, Sudan; Wu, Yiyuan; Sun, Zhijian; Luo, Lusong; Li, Jiajun; Zhang, Hongjian; Zhang, Xiaohu; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6855 – 6868;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

6-Methoxy-1,2,3,4-tetrahydroisoquinoline, cas is 42923-77-3, it is a common heterocyclic compound, the tetrahydroisoquinoline compound, its synthesis route is as follows.

EXAMPLE 42D 1,2,3,4-tetrahydro-6-isoquinolinol A solution of boron tribromide (1.2 mL, 12.5 mmol) in dichloromethane (12.5 mL) was added dropwise to a -78 C. solution of 6-methoxytetrahydroisoquinoline (1.0 g, 5.0 mol, prepared as described in Org. Synth 1988, 67, 60) in dichloromethane (38 mL) The mixture was stirred for 1 hour, warmed to 0 C., stirred for 1 hour, warmed to room temperature, and stirred for 1 hour. The mixture was cooled to -78 C., treated dropwise with methanol (20 mL), warmed to room temperature, stirred for 1 hour, and concentrated to provide the desired product. MS (DCI/NH3) m/e 150 (M+H)+.

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Reference£º
Patent; Bruncko, Milan; McClellan, William J.; US6504031; (2003); B1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem