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Quality Control of [ 115955-90-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 115955-90-3 ]

Product Details of [ 115955-90-3 ]

CAS No. :	115955-90-3	MDL No. :	MFCD02684185
Formula :	C₉H₁₂N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZSHCQIHYOFRGNI-UHFFFAOYSA-N
M.W :	148.21	Pubchem ID :	16217499
Synonyms :

Safety of [ 115955-90-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 115955-90-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 115955-90-3 ]
Downstream synthetic route of [ 115955-90-3 ]

[ 115955-90-3 ] Synthesis Path-Upstream 1~4

1
[ 1125-60-6 ]
[ 115955-90-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 8, p. 2085 - 2094
[2] Patent: US5580872, 1996, A,
[3] Patent: US4812573, 1989, A,
[4] Patent: WO2014/160668, 2014, A1, . Location in patent: Page/Page column 357
[5] Applied Catalysis A: General, 2018, vol. 560, p. 37 - 41

2
[ 1532-72-5 ]
[ 115955-90-3 ]

Reference： [1] Yakugaku Zasshi, 1953, vol. 73, p. 666[2] Chem.Abstr., 1954, p. 7014

3
[ 57554-78-6 ]
[ 1125-60-6 ]
[ 115955-90-3 ]

Reference： [1] Yakugaku Zasshi, 1953, vol. 73, p. 666[2] Chem.Abstr., 1954, p. 7014

4
[ 115955-90-3 ]
[ 24424-99-5 ]
[ 201150-73-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃;	To a solution of 5-aminotetrahydroisoquinoline (3.68 g, 24.8 mmol) in 1,4-dioxane (100 mL) was added 3 N NaOH (8. 27 mL, 24.8 mmol). After cooling to 0 °C, (Boc) 20 (5.42 g, 24.8 mmol) in 1,4-dioxane (10 mL) was added drop-wise and stirred for overnight at room temperature. The reaction mixture was poured into water and extracted with EtOAc (2x). The combined organic layers was washed with sat. aq. NaHC03 solution, water, and brine, then dried and concentrated. The residue was purified by silica gel column chromatography to give 5.44 g (88percent) of the desired Boc-protected product as a white solid
2.4 g	With sodium hydroxide In 1,4-dioxane; water	334B. tert-Butyl 5-amino-3,4-dihydroisoquinoline-2(lH)-carboxylate: 334A was dissolved in dioxane (20 mL) and 1M NaOH (12.62 mL, 12.62 mmol) and B0C₂O was added (2.26 mL, 9.71 mmol). The organic solvent was evaporated and the remaining aqueous was diluted with water (20 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (2 x 20mL) and the combined organic layers were washed with brine (15 mL) and dried (MgS0₄), and evaporated to give 334B (2.4 g) as a light pink solid. NMR (400MHz, chloroform-d) δ 7.04 (t, J = 7.7 Hz, 1H), 6.70 - 6.52 (m, 2H), 4.57 (s, 2H), 3.76 - 3.72 (m, 2H), 2.59 (t, J = 5.9 Hz, 2H), 1.54 - 1.45 (m, 9H) ppm.

Reference： [1] Patent: WO2005/37214, 2005, A2, . Location in patent: Page/Page column 121-122
[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 8, p. 2085 - 2094
[3] Patent: WO2014/160668, 2014, A1, . Location in patent: Page/Page column 357

[ 115955-90-3 ] Synthesis Path-Downstream 1~10

1
[ 1125-60-6 ]
[ 115955-90-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With hydrogen In n-heptane at 150℃; for 72h; Sealed tube; chemoselective reaction;
6.45 g	With sulfuric acid; hydrogen In acetic acid for 20h;
	In methanol	265.a Step 265a. Step 265a. 5-amino-1,2,3,4-tetrahydroisoquinoline A 1.0 g (0.69 mmol) sample of 5-aminoisoquinoline (Aldrich Chemical Co.) was dissolved in 100 mL of methanol and reduced with 250 mg PtO2 catalyst at 25° C. under 4 atmospheres of H2 for 8 hours. The catalyst was removed by filtration, the solvent was removed on a rotary evaporator, and the residue was dried under vacuum to give 1.01 g of crude product. The material was crystallized from i-propanol and dried under vacuum, yield 602 mg. mp=153°-154° C. MS M/Z: 149 (M+H)+, 166 (M+NH4)+.

	In acetic acid	9.a 4-[5-(Phenylsulphonamido)-1,2,3,4-tetrahydroisoquinolin-2-yl]butyric acid hydrochloride (a) A solution of 5-aminoisoquinoline (20 g) in glacial acetic acid (500 ml) was shaken under hydrogen in the presence of a platinum oxide catalyst (2.0 g) at room temperature and approximately 345 kilopascals pressure until uptake of hydrogen stopped. The catalyst was removed by filtration and the filtrate was evaporated to a small volume under reduced pressure. Residual solvent was removed by co-evaporation with water, then isopropyl alcohol, and the resulting solid was recrystallized from isopropyl alcohol to give 5-amino-1,2,3,4-tetrahydroisoquinoline as a white solid, 19 g, m.p. 153°-154° C.
	With platinum(IV) oxide; hydrogen In ethanol	334.A 334A. l,2,3,4-Tetrahydroisoquinolin-5-amine: 334A. l,2,3,4-Tetrahydroisoquinolin-5-amine: Isoquinolin-5 -amine (1.4 g, 9.71 mmol) was hydrogenated in the presence of Ρ( in EtOH (100 mL). The reaction mixture was filtered and concentrated to give 335A. MS (ESI) m/z: 149.0 (M+H)+.
	With hydrogen In pentan-1-ol; water at 130℃; for 2h; Autoclave;	Hydrogenation of quinolines and isoquinolines General procedure: In a typical experiment, the above-prepared thermoregulated phasetransferPt nanocatalyst, n-decane (100 mg) and a certain amount ofsubstrates were added in the autoclave. Then the reactor was replacedthree times with 2 MPa H2 and stirred under hydrogen pressure at adesignated temperature for an appointed time. After reaction, the reactorwas cooled to room temperature and depressurized. The upperproduct phase was easily separated from the lower catalyst phase anddirectly analysed by GC and GC-MS.

Reference： [1]Antil, Neha; Kumar, Ajay; Akhtar, Naved; Begum, Wahida; Chauhan, Manav; Newar, Rajashree; Rawat, Manhar Singh; Manna, Kuntal [Inorganic Chemistry, 2022, vol. 61, # 2, p. 1031 - 1040]
[2]Chan, Wai N.; Hadley, Michael S.; Harling, John D.; Herdon, Hugh J.; Orlek, Barry S.; Riley, Graham J.; Stead, Rachel E. A.; Stean, Tania O.; Thompson, Mervyn; Upton, Neil; Ward, Robert W. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 8, p. 2085 - 2094]
[3]Current Patent Assignee: ABBOTT LABORATORIES INC - US5580872, 1996, A
[4]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4812573, 1989, A
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2014/160668, 2014, A1 Location in patent: Page/Page column 357
[6]Xue, Xiuru; Zeng, Min; Wang, Yanhua [Applied Catalysis A: General, 2018, vol. 560, p. 37 - 41]

2
[ 115955-90-3 ]
[ 24424-99-5 ]
[ 201150-73-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide; In 1,4-dioxane; water; at 0 - 20℃;	To a solution of 5-aminotetrahydroisoquinoline (3.68 g, 24.8 mmol) in 1,4-dioxane (100 mL) was added 3 N NaOH (8. 27 mL, 24.8 mmol). After cooling to 0 C, (Boc) 20 (5.42 g, 24.8 mmol) in 1,4-dioxane (10 mL) was added drop-wise and stirred for overnight at room temperature. The reaction mixture was poured into water and extracted with EtOAc (2x). The combined organic layers was washed with sat. aq. NaHC03 solution, water, and brine, then dried and concentrated. The residue was purified by silica gel column chromatography to give 5.44 g (88%) of the desired Boc-protected product as a white solid
2.4 g	With sodium hydroxide; In 1,4-dioxane; water;	334B. tert-Butyl 5-amino-3,4-dihydroisoquinoline-2(lH)-carboxylate: 334A was dissolved in dioxane (20 mL) and 1M NaOH (12.62 mL, 12.62 mmol) and B0C2O was added (2.26 mL, 9.71 mmol). The organic solvent was evaporated and the remaining aqueous was diluted with water (20 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (2 x 20mL) and the combined organic layers were washed with brine (15 mL) and dried (MgS04), and evaporated to give 334B (2.4 g) as a light pink solid. NMR (400MHz, chloroform-d) delta 7.04 (t, J = 7.7 Hz, 1H), 6.70 - 6.52 (m, 2H), 4.57 (s, 2H), 3.76 - 3.72 (m, 2H), 2.59 (t, J = 5.9 Hz, 2H), 1.54 - 1.45 (m, 9H) ppm.

Reference： [1]Patent: WO2005/37214,2005,A2 .Location in patent: Page/Page column 121-122
[2]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2085 - 2094
[3]Patent: WO2014/160668,2014,A1 .Location in patent: Page/Page column 357

3
[ 115955-90-3 ]
[ 142770-42-1 ]
[ 1351934-63-8 ]

Reference： [1]Biochemical Pharmacology,2012,vol. 83,p. 57 - 68

4
[ 115955-90-3 ]
[ 69812-51-7 ]
[ 1581289-02-2 ]

Yield	Reaction Conditions	Operation in experiment
41%	With triethylamine; In dichloromethane; at 20℃; for 2h;	General procedure: To the solution of the appropriate amine (1 mmol) in 5ml of CH2Cl2, the corresponding aromatic sulfonyl chloride(1 mmol) was added, followed by the addition of one equivalent of TEA. The resulting mixture was stirred for 2 h at ambient temperature, monitored by TLC (n-hexane/ethyl acetate= 2:1). Next, 5 ml of water was poured into the reaction mixture and extracted by EtOAc (2x20mL). The collected organic phase was dried over anhydrous Na2SO4, filtered and evaporated to dryness. Crude products were purified by either flash chromatography (n-hexane/EtOAc) or recrystallization(EtOH).

Reference： [1]Medicinal Chemistry,2013,vol. 9,p. 911 - 919

5
[ 115955-90-3 ]
[ 39234-86-1 ]
[ 1581289-15-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine; In dichloromethane; at 20℃; for 2h;	General procedure: To the solution of the appropriate amine (1 mmol) in 5ml of CH2Cl2, the corresponding aromatic sulfonyl chloride(1 mmol) was added, followed by the addition of one equivalent of TEA. The resulting mixture was stirred for 2 h at ambient temperature, monitored by TLC (n-hexane/ethyl acetate= 2:1). Next, 5 ml of water was poured into the reaction mixture and extracted by EtOAc (2x20mL). The collected organic phase was dried over anhydrous Na2SO4, filtered and evaporated to dryness. Crude products were purified by either flash chromatography (n-hexane/EtOAc) or recrystallization(EtOH).

Reference： [1]Medicinal Chemistry,2013,vol. 9,p. 911 - 919

6
[ 115955-90-3 ]
[ 705-21-5 ]
[ 1581289-18-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; In dichloromethane; at 20℃; for 2h;	General procedure: To the solution of the appropriate amine (1 mmol) in 5ml of CH2Cl2, the corresponding aromatic sulfonyl chloride(1 mmol) was added, followed by the addition of one equivalent of TEA. The resulting mixture was stirred for 2 h at ambient temperature, monitored by TLC (n-hexane/ethyl acetate= 2:1). Next, 5 ml of water was poured into the reaction mixture and extracted by EtOAc (2x20mL). The collected organic phase was dried over anhydrous Na2SO4, filtered and evaporated to dryness. Crude products were purified by either flash chromatography (n-hexane/EtOAc) or recrystallization(EtOH).

Reference： [1]Medicinal Chemistry,2013,vol. 9,p. 911 - 919

7
[ 5344-90-1 ]
[ 115955-90-3 ]
4-amino-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With oxygen In para-xylene at 130℃; for 10h;	15 Example 15 The preparation of the catalyst was as described in Example 1. In the reaction flask was added 35 mg of the catalyst with a calcination temperature of 800 , 1 ml of p-xylene as the solvent, 0.3 mmol of 5-amino-1,2,3,4-tetrahydroisoquinoline and 0.25mmol 2-aminobenzyl alcohol, the reactor is filled with 0.1MPa O2, Reacted at 130 for 10h, NMR quantitatively obtained 4-amino-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-one, the yield was 66%
54%	With oxygen; 4-nitro-benzoic acid In para-xylene at 120℃; for 16h; chemoselective reaction;

Reference： [1]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN112876470, 2021, A Location in patent: Paragraph 0004
[2]Xie, Feng; Chen, Qing-Hua; Xie, Rong; Jiang, Huan-Feng; Zhang, Min [ACS Catalysis, 2018, vol. 8, # 7, p. 5869 - 5874]

8
[ 607-32-9 ]
[ 115955-90-3 ]
C₁₈H₁₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 73.1% 2: 24.9%	With hydrogen In tetrahydrofuran at 40℃; Flow reactor;

Reference： [1]Duan, Xiaonan; Wang, Xuepeng; Chen, Xingkun; Zhang, Jisong [Organic Process Research and Development, 2021, vol. 25, # 9, p. 2100 - 2109]

9
[ 607-32-9 ]
[ 1125-60-6 ]
[ 115955-90-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 86.4% 2: 13.4%	With 1 % platinum on carbon; hydrogen In tetrahydrofuran at 40℃; Flow reactor;

Reference： [1]Duan, Xiaonan; Wang, Xuepeng; Chen, Xingkun; Zhang, Jisong [Organic Process Research and Development, 2021, vol. 25, # 9, p. 2100 - 2109]

10
[ 607-32-9 ]
[ 1125-60-6 ]
[ 115955-90-3 ]
C₉H₁₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 64.9% 2: 27.8% 3: 6.8%	With 1 % platinum on carbon; hydrogen In tetrahydrofuran at 110℃; Flow reactor;
1: 41.615% 2: 39.3% 3: 19.1%	With 1 % platinum on carbon; hydrogen In tetrahydrofuran at 150℃; Flow reactor;

Reference： [1]Duan, Xiaonan; Wang, Xuepeng; Chen, Xingkun; Zhang, Jisong [Organic Process Research and Development, 2021, vol. 25, # 9, p. 2100 - 2109]
[2]Duan, Xiaonan; Wang, Xuepeng; Chen, Xingkun; Zhang, Jisong [Organic Process Research and Development, 2021, vol. 25, # 9, p. 2100 - 2109]

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H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 115955-90-3 ] {[proInfo.proName]}

Quality Control of [ 115955-90-3 ]

Related Doc. of [ 115955-90-3 ]

Product Details of [ 115955-90-3 ]

Safety of [ 115955-90-3 ]

Application In Synthesis of [ 115955-90-3 ]

[ 115955-90-3 ] Synthesis Path-Upstream 1~4

[ 115955-90-3 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 115955-90-3 ]

Amines

Related Parent Nucleus of [ 115955-90-3 ]

Tetrahydroisoquinolines

Precautionary Statements-General

Prevention

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Physical hazards

Health hazards

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Related Functional Groups of
[ 115955-90-3 ]

Related Parent Nucleus of
[ 115955-90-3 ]