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Chemical Structure| 345264-61-1 Chemical Structure| 345264-61-1

Structure of 345264-61-1

Chemical Structure| 345264-61-1

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Product Details of [ 345264-61-1 ]

CAS No. :345264-61-1
Formula : C9H10FN
M.W : 151.18
SMILES Code : FC1=CC=CC2=C1CCCN2
English Name :5-Fluoro-1,2,3,4-tetrahydroquinoline
MDL No. :MFCD08544259

Safety of [ 345264-61-1 ]

Application In Synthesis of [ 345264-61-1 ]

* 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 [ 345264-61-1 ]

[ 345264-61-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 394-69-4 ]
  • 5-fluoro-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With hydrogen;5%-palladium/activated carbon; In methanol; at 40℃; under 3102.97 Torr; Reduction; Shake a mixture of <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (28.1 g) and 5percent palladium on carbon (5.6 g) in methanol over night at 40°C under 60 psi hydrogen. Filter the mixture through Celite and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5-10percent ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the title compound (22.5 g, 78percent). MS (EI, m/z) CgHloFN (M+1) 152.0
78% With hydrogen;5% palladium over charcoal; In methanol; at 40℃; under 3102.97 Torr;Under hydrogen; Preparation LIII 5-fluoro-1,2,3,4-tetrahydro<strong>[394-69-4]quinoline</strong> [0363] <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> [0364] To a suspension of 5-amino<strong>[394-69-4]quinoline</strong> (50 g, 347 mmol) in 48percent HBF4 (200 mL) at 0° C. was added portionwise sodium nitrite. This was stirred for 1 hour and then poured into 1:1 ethyl acetate/diethyl ether (500 mL). The resulting suspension was filtered and the solid dried. This solid (82.5 g, 338 mmol) was added portionwise to refluxing xylene (1 L) and stirred for 2 hours then allowed to cool. The xylene was decanted off and the residue dissolved in 1N hydrochloric acid (600 mL). After neutralization with sodium carbonate, the mixture was extracted with ethyl acetate (10.x.500 mL). The extracts were dried over sodium sulfate, filtered and the volatiles removed under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10-20percent diethyl ether in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 28.1 g (55percent) of the desired compound. MS (EI, m/z) C9H6FN (M+1) 148.0 [0365] Reduction [0366] A mixture of <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (28.1 g), 5percent palladium on carbon (5.6 g) in methanol was shaken over night at 40° C. under 60 psi hydrogen. The mixture was filtered through celite and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5-10percent ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 22.5 g (78percent) of the title compound. [0367] MS (EI, m/z) C9H10FN (M+1) 152.0
70% With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; Palladium on carbon (10percent, 1.25 g) was added to a solution of <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (2.5 g, 16.99 mmol) in methanol and the reaction was overnight at room temperature under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated in vacuo to afford 5-fluoro-l ,2,3,4-tetrahydro<strong>[394-69-4]quinoline</strong> as a colorless oil (1.80 g, 70 percent).LC/MS (ES, m/z) [M+H]+ 152.0'H-NMR (300 MHz, CDCI3) delta 6.87 - 6.95 (m, 2H), 6.26 - 6.40 (m, 2H), 3.28 - 3.31 (m, 2H), 2.72 - 2.77 (t, / = 6.60 Hz, 2H), 1.92 - 1.98 (m, 2H)
  • 2
  • [ 1095270-78-2 ]
  • [ 345264-61-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-fluoro-2,3-dihydroquinolin-4(1H)-one With triethylsilane; trifluoroacetic acid In trifluoroacetic acid at 20℃; for 16h; Stage #2: With sodium hydroxide In water 4 Synthesis of 5-fluoro-1,2,3,4-tetrahydroquinoline To a solution of 5-fluoro-2,3-dihydro-1H-quinolin-4-one obtained in Reference Example 3 (64 mg) in trifluoroacetic acid (5 ml), triethylsilane (0.37 ml) was added and stirred at room temperature for 16 hours. After distilling off the solvent under reduced pressure, the residue was diluted with water, adjusted to pH 11 by addition of 1M aqueous sodium hydroxide, and extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluding solvent: n-hexane:ethyl acetate = 3:1). The resulting residue was diluted with chloroform, added to 1M aqueous hydrochloric acid (15 ml) and partitioned. The aqueous layer was adjusted to pH 11 by addition of 2.5M aqueous sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure to give the titled compound, i.e., 5-fluoro-1,2,3,4-tetrahydroquinoline (39 mg) as a light-yellow oil.
  • 3
  • [ 345264-61-1 ]
  • [ 20098-19-5 ]
  • [ 530-62-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Stage #1: E-4-aminoadamantan-1-ol hydrochloride; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 5-fluoro-1,2,3,4-tetrahydroquinoline With dmap In N,N-dimethyl-formamide at 120℃; for 11h; 1 Synthesis of 5-fluoro-N-(E-1-hydroxyadamantan-4-yl)-3,4-dihydroquinoline-1(2H)-carboxamide (Compound 1) To a solution of E-4-aminoadamantan-1-ol hydrochloride obtained in Reference Example 1 (79 mg) in N,N-dimethylformamide (3 ml), triethylamine (0.13 ml) and N,N'-carbonyldiimidazole (69 mg) were added and stirred at room temperature for 1 hour. To the reaction mixture, a solution of 5-fluoro-1,2,3,4-tetrahydroquinoline obtained in Reference Example 4 (39 mg) in N,N-dimethylformamide (2 ml) was then added and heated to 120°C, followed by stirring for 8 hours. To the reaction mixture, N,N-dimethylaminopyridine (3 mg) was added and stirred at 120°C for an additional 3 hours. After cooling at room temperature, the reaction mixture was poured into 1M aqueous hydrochloric acid and extracted with ethyl acetate. The extracted organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the desiccant was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluding solvent: chloroform:methanol = 97:3 to 19:1) to give the titled compound (Compound 1, 17 mg) as a colorless powder. 1H NMR (300 MHz, CHLOROFORM-D) δ 1.25-1.55 (m, 5 H), 1.71-1.79 (m, 4 H), 1.85-1.97 (m, 4 H), 2.08-2.18 (m, 3 H), 2.75-2.82 (m, 2 H), 3.74-3.80 (m, 2 H), 3.93-4.00 (m, 1 H), 5.41-5.48 (m, 1 H), 6.77-6.84 (m, 1 H), 7.10-7.21 (m, 2 H).
  • 4
  • [ 611-34-7 ]
  • [ 345264-61-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium nitrite; tetrafluoroboric acid / xylene / 0 °C / Reflux 2: hydrogen / 10% Pd/C / methanol / 20 °C
  • 5
  • [ 345264-61-1 ]
  • [ 1384852-13-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 2.1: pyridine / dichloromethane / 20 °C / Inert atmosphere 3.1: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 95 °C / Inert atmosphere 4.1: sodium hydroxide; water / methanol / 20 °C 4.2: pH 5
  • 6
  • [ 345264-61-1 ]
  • [ 1384850-71-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 2: pyridine / dichloromethane / 20 °C / Inert atmosphere
  • 7
  • [ 345264-61-1 ]
  • [ 1384852-14-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-methyl-pyrrolidin-2-one / 1 h / 150 °C 2: pyridine / dichloromethane / 20 °C / Inert atmosphere 3: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 1 h / 95 °C / Inert atmosphere
  • 8
  • [ 345264-61-1 ]
  • [ 1384850-39-8 ]
  • [ 1384850-70-7 ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one at 150℃; for 1h; 19.3 To a solution of methyl 3-chloro-2-oxo-l,2-dihydroquinoxaline-6-carboxylate (1.0 g, 4.19 mmol) in NMP (10.0 mL) was added 5-fluoro-l,2,3,4-tetrahydroquinoline (1.5 g, 9.92 mmol) with Attorney Docket No. BIOE0009-401-PCstirring for 1 h at 150°C in an oil bath. The reaction mixture was cooled to room temperature, precipitated with water (100 mL). The solids were collected by filtration and dried in an oven under reduced pressure to afford methyl 3-(5-fluoro-l,2,3,4-tetrahydroquinolin-l-yl)-2-oxo-l ,2- dihydroquinoxaline-6-carboxylate as a gray solid (1.0 g, crude).LC/MS (ES, m/z): [M+H]+ 354.0
 

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