[ CAS No. 97112-03-3 ] {[proInfo.proName]}

Name: 97112-03-3|5,6,7,8-Tetrahydroisoquinolin-5-ol|95%
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SKU: A423387
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Quality Control of [ 97112-03-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 97112-03-3 ]

CAS No. :	97112-03-3	MDL No. :	MFCD11847763
Formula :	C₉H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FZUMQCKAVKSWLQ-UHFFFAOYSA-N
M.W :	149.19	Pubchem ID :	10855632
Synonyms :

Safety of [ 97112-03-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 97112-03-3 ]

* 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 [ 97112-03-3 ]
Downstream synthetic route of [ 97112-03-3 ]

[ 97112-03-3 ] Synthesis Path-Upstream 1~1

1
[ 97112-03-3 ]
[ 2439-04-5 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35

[ 97112-03-3 ] Synthesis Path-Downstream 1~34

1
[ 50388-20-0 ]
[ 97112-03-3 ]

Yield	Reaction Conditions	Operation in experiment
34%		REFERENCE EXAMPLE 2; 5,6,7,8-Tetrahydroisoquinolin-5-ol; A solution of 5,6,7,8-tetrahydroisoquinoline lambda/-oxide (56.00 g, 0.38 mol, obtained in reference example 1 ) in Ac2O (100 imL) was added dropwise over Ac2O (76 imL) previously heated to reflux. Once the addition was finished, it was stirred at reflux for 90 min and allowed to cool to room temperature. The solvent was evaporated. <n="34"/>CHCI3 and water were added and the phases were separated. The aqueous phase was reextracted 2 times with CHCI3. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. 12% HCI (375 ml_) was added to the obtained residue and it was heated at reflux for 5h. It was allowed to cool and the pH was adjusted at 7 with 2 N NaOH. The aqueous phase was extracted with CHCI3. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 18.94 g of the desired compound (yield: 34%). 1 H NMR (300 MHz, CDCI3) delta (TMS): 1.79 (m, 2 H), 1.90 - 2.16 (complex signal, 2 H), 2.76 (m, 2 H), 3.30 (broad s, 1 H, OH), 4.74 (m, 1 H), 7.38 (d, J = 5.1 Hz, 1 H), 8.33 (s, 1 H), 8.37 (d, J = 5.1 Hz, 1 H).
	With hydrogenchloride; In acetic anhydride;	(283-2) 5,6,7,8-Tetrahydroisoquinolin-5-ol 5,6,7,8-Tetrahydroisoquinoline-2-oxide (7.50 g) was dissolved in acetic anhydride (30 ml). After reacting at 120 C. for 6 hr, the reaction solution was concentrated under reduced pressure. Next, a 10% aqueous solution (30 ml) of hydrochloric acid was added to the residue followed by heating at 100 C. for 2 hr. The reaction solution was cooled, basified with 5N sodium hydroxide and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried. After evaporating the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.90 g).

Reference： [1]Patent: WO2007/60198,2007,A1 .Location in patent: Page/Page column 32-33
[2]Journal of the Chemical Society. Perkin transactions I,1985,p. 213 - 220
[3]Tetrahedron,1996,vol. 52,p. 10935 - 10944
[4]Journal of the Chemical Society. Perkin transactions I,1992,p. 31 - 35
[5]Patent: US2002/19531,2002,A1
[6]RSC Advances,2018,vol. 8,p. 6356 - 6364

2
[ 97112-03-3 ]
[ 21917-86-2 ]

Yield	Reaction Conditions	Operation in experiment
89%		REFERENCE EXAMPLE 3; 7,8-Dihydro-6/-/-isoquinolin-5-one; To a solution of oxalyl chloride (1.9 ml_, 22 mmol) in CH2CI2 (80 ml_) under argon and previously cooled at -50/-600C, a solution of DMSO (3.1 ml_, 44 mmol) in CH2CI2 (10 imL) was added. It was stirred for 5 min at -50/-600C and a solution of <strong>[97112-03-3]5,6,7,8-tetrahydroisoquinolin-5-ol</strong> (3.00 g, 20 mmol, obtained in reference example 2) in CH2CI2 (20 ml_) was added. After stirring for 15 min at -50/-600C, TEA (13.9 mL, 100 mmol) was added. It was stirred for 5 min at -50/-600C and allowed to warm to room temperature. It was poured over a mixture of water-ice. It was extracted 3 times with CH2CI2. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 2.63 g of the desired compound as an orange liquid (yield: 89%).LC-MS (method 1 ): tR = 2.52 min; m/z = 148.0 [M+H]+.

Reference： [1]Patent: WO2007/60198,2007,A1 .Location in patent: Page/Page column 33
[2]RSC Advances,2018,vol. 8,p. 6356 - 6364
[3]Journal of the Chemical Society. Perkin transactions I,1985,p. 213 - 220

3
[ 97112-03-3 ]
[ 24334-24-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 31 - 35

4
[ 139484-24-5 ]
[ 97112-03-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 31 - 35
[2]RSC Advances,2018,vol. 8,p. 6356 - 6364
[3]Tetrahedron,1996,vol. 52,p. 10935 - 10944

5
[ 97112-03-3 ]
[ 74-88-4 ]
[ 181418-47-3 ]