1,2,3,4-Tetrahydroquinoline | Tetrahydroquinolines

CAS No. :	635-46-1
Formula :	C₉H₁₁N
M.W :	133.19
SMILES Code :	C12=C(NCCC2)C=CC=C1
MDL No. :	MFCD00006693
InChI Key :	LBUJPTNKIBCYBY-UHFFFAOYSA-N
Pubchem ID :	69460

Safety of 1,2,3,4-Tetrahydroquinoline

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302+H312+H332-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of 1,2,3,4-Tetrahydroquinoline

* 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.

Downstream synthetic route of [ 635-46-1 ]

[ 635-46-1 ] Synthesis Path-Downstream 1~20

1
[ 635-46-1 ]
[ 22358-80-1 ]
[ 3973-08-8 ]

References: [1]Helvetica Chimica Acta,1948,vol. 31,p. 924,925.

2
[ 635-46-1 ]
[ 58929-72-9 ]
bis-[3-(3,4-dihydro-2<i>H</i>-[1]quinolyl)-propyl]-ether [ No CAS ]

References: [1]Journal Of Scientific and Industrial Research,1953,vol. 12B,p. 532,533,534.

3
[ 635-46-1 ]
[ 58196-33-1 ]
[ 61468-43-7 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 4565 - 4568.

4
[ 635-46-1 ]
[ 1186-73-8 ]
[ 193754-21-1 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 969 - 972.
[2]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 627 - 636.

5
[ 635-46-1 ]
[ 134221-52-6 ]
[ 202463-43-2 ]

References: [1]Tetrahedron,1998,vol. 54,p. 927 - 934.

6
[ 635-46-1 ]
[ 97-08-5 ]
[ 847170-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20℃;	Reference Example 1 1-[(4-Chloro-3-nitrophenyl)sulfonyl]-1,2,3,4-tetrahydroquinoline A solution of 4-chloro-3-nitrobenzenesulfonyl chloride (17.0 g) in THF (50 ml) was added to 1,2,3,4-tetrahydroquinoline (9.74 g) and sodium hydrogencarbonate (8.38 g) with stirring in THF (150 ml) and water (15 ml) at room temperature, and the mixture was further stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained crystals were washed with diisopropyl ether to give the object (15.7 g) as crystals. 1H-NMR (CDCl3) delta 1.66-1.78 (2H, m), 2.49 (2H, t), 3.85 (2H, t), 7.03-7.07 (1H, m), 7.14 (1H, dt), 7.23-7.27 (1H, m), 7.57 (1H, d), 7.63 (1H, dd), 7.74-7.78 (1H, m), 8.08 (1H, d).
	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20℃;	Reference Example 1; 2-Chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)aniline; To a suspension of 1,2,3,4-tetrahydroquinoline(3.12 g) and sodium hydrogen carbonate (2.66 g) in tetrahydrofuran (60 mL) were added water (6 mL) and a solution of 4-chloro-3-nitrobenzenesulfonyl chloride (5.4 g) in tetrahydrofuran (30 mL) successively, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with water, 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 1-[(4-chloro-3-nitrophenyl)sulfonyl]-1,2,3,4-tetrahydroquinoline (5.0 g). This material was dissolved in tetrahydrofuran (45 mL). To the solution were added methanol (45 mL), nickel(II) bromide (0.15 g) and sodium borohydride (1.61 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. Then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1) to give the title compound (4.33 g).
	With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20℃;	Reference Example 12 2-Chloro-5-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)aniline To a suspension of 1,2,3,4-tetrahydroquinoline (3.12 g) and sodium hydrogen carbonate (2.66 g) in tetrahydrofuran (60 mL) were added water (6 mL) and a solution of 4-chloro-3-nitrobenzenesulfonyl chloride (5.4 g) in tetrahydrofuran (30 mL) successively, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with water, 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 1-[(4-chloro-3-nitrophenyl)-sulfonyl]-1,2,3,4-tetrahydroquinoline (5.0 g). This material was dissolved in tetrahydrofuran (45 mL). To the solution were added methanol (45 mL), nickel(II) bromide (0.15 g) and sodium borohydride (1.61 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes, and then stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 3/1) to give the title compound (4.33 g).

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 273 - 275.
[2]Patent: EP1847541,2007,A1 .Location in patent: Page/Page column 62.
[3]Patent: EP1939204,2008,A1 .Location in patent: Page/Page column 15.
[4]Patent: EP2143724,2010,A1 .Location in patent: Page/Page column 24-25.

7
[ 635-46-1 ]
[ 107819-90-9 ]
N¹,N²-bis(tert-butoxycarbonyl)-3,4-dihydro-2H-quinoline-1-carboxamidine [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 2300 - 2309.

8
[ 401564-36-1 ]
[ 635-46-1 ]
3-[(2S,4S)-1-tert-butoxycarbonyl-4-(1,2,3,4-tetrahydro-1-quinolyl)-2-pyrrolidinylcarbonyl]-1,3-thiazolidine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 641 - 655.

9
[ 635-46-1 ]
[ 114744-51-3 ]

References: [1]European Journal of Organic Chemistry,2010,p. 3593 - 3610.

10
[ 635-46-1 ]
[ 98556-31-1 ]
[ 1373622-00-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	In 1,4-dioxane; at 110℃; for 3h;	7.1 Preparation of 4-(3,4-dihydro-2H-quinolin-1-yl)-6-iodoquinazoline 1.30 g of <strong>[98556-31-1]4-chloro-6-iodoquinazoline</strong>, 1.50 ml of 1,2,3,4-tetrahydroquinoline in 10 ml of dioxane are heated at 110 C. in a flask until the quinazoline has reacted completely (HPLC check, about 3 hours). The cooled reaction solution is diluted with EA and washed 3 times with 5% citric acid. The organic phase is dried over sodium sulfate and purified by means of column chromatography (gradient heptane: EA 0-100% in 18 min.), giving 1.27 g of 4-(3,4-dihydro-2H-quinolin-1-yl)-6-iodoquinazoline as yellowish solid (yield 81%, content 99%); MS-FAB (M+H+)=388.0; Rf (polar method): 2.89 min.

References: [1]Patent: US2013/210819,2013,A1 .Location in patent: Paragraph 0276-0277.

11
[ 635-46-1 ]
[ 399-25-7 ]
6-(1-(2-fluorophenyl)-2-nitroethyl)-1,2,3,4-tetrahydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With indium(III) chloride; In water; at 100℃;	General procedure: A 5 ml RB flask containing 1,2,3,4-tetrahydroquinoline (1) (1.0 mmol), β-nitrostyrene 3 (1.0mmol) and water (2 mL) was placed in oil bath and heated at 100 oC (temperature monitored by a thermometer). After the reaction was completed, the aqueous mixture was extracted with ethyl acetate and dried over Na2SO4, and the solvent was removed under reduced pressure. The progress of reaction was monitored by TLC. The reaction mixture was purified by (silica gel)column chromatography (pentane/AcOEt, 80:20 as eluent) to give pure products.

References: [1]Synthesis,2017,vol. 49,p. 3171 - 3182.

12
[ 4965-36-0 ]
[ 635-46-1 ]
[ 114744-51-3 ]

References: [1]ACS Catalysis,2018,vol. 8,p. 4545 - 4557.

13
[ 635-46-1 ]
[ 67-66-3 ]
[ 128742-76-7 ]
methyl 1-methyl-3-(1,2,3,4-tetrahydroquinoline-1-carbonyl)-1H-indole-5-carboxylate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 3928 - 3935.

14
[ 635-46-1 ]
[ 70639-77-9 ]
6-(3,4-dihydro-2H-quinoline-1-carbonyl)-3,4-dihydro-1H-quinolin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-Methylpyridine; methanesulfonyl chloride; In acetonitrile; at 0 - 25℃; for 16.0h;	To a stirred solution of <strong>[70639-77-9]2-oxo-3,4-dihydro-1H-quinoline-6-carboxylic acid</strong> (300 mg) and 1,2,3,4-tetrahydroquinoline 90 (0.3 ml) in acetonitrile (5 ml) at 0 C were added sequentially 3-methylpyridine (731 mg) and methanesulfonyl chloride (360 mg). The reaction mixture was warmed to 25 C and stirred at 25 C for 16 hours. The solution was diluted with water (5 ml) and was extracted with ethyl acetate (3 x 5 ml). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified bypreparative HPLC to afford 6-(3 ,4-dihydro-2H-quinoline- 1 -carbonyl)-3 ,4-dihydro- 1H-quinolin-2-one as a yellow solid. MS (ISP): 293.1 ([M+H]j.

References: [1]Patent: WO2019/43208,2019,A1 .Location in patent: Page/Page column 86.

15
[ 635-46-1 ]
[ 2001-32-3 ]

References: [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4970 - 4974.

16
[ 635-46-1 ]
[ 91-22-5 ]
[ 3373-00-0 ]

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 9551 - 9555.
Angew. Chem.,2019,vol. 131,p. 9651 - 9655,5.

17
[ 635-46-1 ]
[ 91-22-5 ]
[ 3373-00-0 ]
1,2,3,4-tetrahydro-2,3'-biquinoline [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 9551 - 9555.
Angew. Chem.,2019,vol. 131,p. 9651 - 9655,5.

18
[ 635-46-1 ]
[ 91-22-5 ]
[ 553-03-7 ]
[ 3373-00-0 ]
1,2,3,4-tetrahydro-2,3'-biquinoline [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 9551 - 9555.
Angew. Chem.,2019,vol. 131,p. 9651 - 9655,5.

19
[ 635-46-1 ]
[ 91-22-5 ]
[ 52851-41-9 ]
3,4-dihydroisoquinoline [ No CAS ]

References: [1]New Journal of Chemistry,2019,vol. 43,p. 18702 - 18712.

20
[ 635-46-1 ]
[ 129112-65-8 ]
2-chloro-4-(3,4-dihydroquinolin-1(2H)-yl)-7-nitroquinazoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 1.0h;	To a solution of <strong>[129112-65-8]2,4-dichloro-7-nitroquinazoline</strong> (500 mg, 2.049 mmol) in DMF (3.1 mL) were added 1,2,3,4-tetrahydroquinoline (273 mg, 2.049 mmol) and sodium hydride (49.2 mg, 2.049 mmol), and the mixture was stirred for 1 h at RT. The reaction mixture was diluted with AcOEt, washed successively with water and brine, and dried over Na2SO4. The organic layer was concentrated in vacuo. The residue was used for the next step without further purification. LCMS(m/z) 341.03 [M+H]+.

References: [1]Patent: WO2021/130638,2021,A1 .Location in patent: Paragraph 1374.

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Product Details of 1,2,3,4-Tetrahydroquinoline

Safety of 1,2,3,4-Tetrahydroquinoline

Application In Synthesis of 1,2,3,4-Tetrahydroquinoline

[ 635-46-1 ] Synthesis Path-Downstream 1~20

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