* 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.
With diethylazodicarboxylate In chloroform; toluene at 20℃; for 12 h;
General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1,2,3,4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wtpercent in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHCl3 (1.0 mL) was added. The reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with EtOAc:hexane (1:5) to give quinolines. In case of 2f and 2m, the product spot was close to the spot of the remained DEAD. To eliminate the remained DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred.[19] After 10 min, the reaction mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with CHCl3:hexane (1:1) to give quinolines.
68%
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen In N,N-dimethyl-formamide for 12 h;
General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for 1H and 100 MHz for 13C, using CDCl3 as solvent with TMS as the internal standard. Thin-layer chromatography was performed on silica gel 60 F254 (Sinopharm) thin-layer chromatography plates using petroleum ether/ethyl acetate (10:1 v/v) as the mobile phase.
Reference:
[1] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3080 - 3084[3] Angew. Chem., 2017, vol. 129, # 11, p. 3126 - 3130,5
[4] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[5] Synthetic Communications, 2018, vol. 48, # 11, p. 1291 - 1298
[6] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14167 - 14172
[7] Organic Letters, 2018, vol. 20, # 20, p. 6436 - 6439
[8] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[9] Patent: CN107141252, 2017, A, . Location in patent: Paragraph 0048; 0049; 0050; 0051; 0052
2
[ 56-81-5 ]
[ 371-40-4 ]
[ 396-30-5 ]
Reference:
[1] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
[2] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 16967 - 16970,4
[3] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 16967 - 16970
[4] Journal of Molecular Structure, 2003, vol. 661-662, # 1-3, p. 209 - 218
[5] Patent: WO2009/87649, 2009, A1, . Location in patent: Page/Page column 24
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 41, p. 12891 - 12894[7] Angew. Chem., 2016, vol. 128, p. 13083 - 13086,4
3
[ 1227828-28-5 ]
[ 396-30-5 ]
Yield
Reaction Conditions
Operation in experiment
60%
With Selectfluor; barium(II) oxide; silver(l) oxide In acetone at 23 - 90℃; for 2 h;
To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (69.6 mg, 0.300 mmol, 3.00 equiv), barium oxide (17.2 mg, 0.110 mmol, 1.10 equiv), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial. The reaction mixture was cooled to 23 °C, passed through a pad of Celite and concentrated under reduced pressure. To the residue was added CH2Cl2 (20 mL) and a saturated aqueous solution of NaHCO3 (20 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on preparative TLC.
Reference:
[1] Science, 2009, vol. 325, # 5948, p. 1661 - 1664
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 1662 - 1663
[3] Tetrahedron, 2011, vol. 67, # 24, p. 4449 - 4454
5
[ 580-15-4 ]
[ 396-30-5 ]
Reference:
[1] Journal of the American Chemical Society, 1949, vol. 71, p. 1785
[2] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 10
6
[ 5332-25-2 ]
[ 396-30-5 ]
Reference:
[1] Applied Catalysis A: General, 2011, vol. 394, # 1-2, p. 191 - 194
7
[ 3054-95-3 ]
[ 371-40-4 ]
[ 396-30-5 ]
Yield
Reaction Conditions
Operation in experiment
29.6 %Chromat.
With Ni-modified Beta zeolite In neat (no solvent) for 0.0833333 h; Microwave irradiation; Reflux; Green chemistry
General procedure: General procedure for synthesis of quinolines from anilines and ADA was carried out in Panasonic NN-K5541JF microwave oven reactor equipping a magnetic stirring device. The typical procedures were as follows: ADA (1mmol), excessive anilines (4mmol) and solid catalyst were charged into a round-bottom ask; and then, the mixtures was placed into microwave reactor. The reaction was conducted by continuous microwave irradiation for 1–40 min under refluxing and stirring condition. Finally, the resulting products were determined by GC–MS of Varian Saturn 2200/ CP-3800 gas chromatography–mass spectrometry equipped with two CP8944 capillary columns (VF-5,30m×0.25mm×0.25 μm).
Reference:
[1] Chemistry - An Asian Journal, 2014, vol. 9, # 11, p. 3089 - 3093
9
[ 107-02-8 ]
[ 371-40-4 ]
[ 396-30-5 ]
Reference:
[1] Chemistry - An Asian Journal, 2014, vol. 9, # 11, p. 3089 - 3093
10
[ 2338-74-1 ]
[ 396-30-5 ]
Reference:
[1] Chemical Communications, 2015, vol. 51, # 32, p. 7035 - 7038
11
[ 580-16-5 ]
[ 396-30-5 ]
Reference:
[1] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11482 - 11484
[2] Patent: WO2012/142162, 2012, A2, . Location in patent: Page/Page column 24
12
[ 91-22-5 ]
[ 396-30-5 ]
[ 394-68-3 ]
[ 394-69-4 ]
[ 16650-32-1 ]
Reference:
[1] Journal of Fluorine Chemistry, 2002, vol. 117, # 2, p. 99 - 101
13
[ 394-70-7 ]
[ 56-81-5 ]
[ 396-30-5 ]
Reference:
[1] Journal of Organic Chemistry, 1951, vol. 16, p. 1450
14
[ 60144-53-8 ]
[ 1611-78-5 ]
[ 396-30-5 ]
Reference:
[1] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7288 - 7291
15
[ 60144-53-8 ]
[ 927-63-9 ]
[ 396-30-5 ]
Reference:
[1] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7288 - 7291
16
[ 91-22-5 ]
[ 396-30-5 ]
[ 394-68-3 ]
[ 394-69-4 ]
[ 16650-32-1 ]
Reference:
[1] Journal of Fluorine Chemistry, 2002, vol. 117, # 2, p. 99 - 101
17
[ 91-22-5 ]
[ 396-30-5 ]
[ 394-68-3 ]
[ 394-69-4 ]
[ 16650-32-1 ]
Reference:
[1] Journal of Fluorine Chemistry, 2002, vol. 117, # 2, p. 99 - 101
18
[ 396-30-5 ]
[ 59611-52-8 ]
Yield
Reaction Conditions
Operation in experiment
71.6%
at 20℃; for 12 h;
Sodium cyanoborohydride (6.45 g, 103 mmol ) was added gradually to the solution of 6-fluoro quinoline (5 g, 34 mmol) in glacial acetic acid (100 ml) at ambient temperature. After stirring for 12 h the reaction mixture was quenched in water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with water, brine and dried over sodium sulfate, filtered and evaporated in vacuo, the residue was purified by a silica gel column with 1 percent to 5percent ethyl acetate in petroleum ether to afford 6-fluoro- 1 , 2,3, 4-tetrahydroquinoline as a light yellow liquid (3.65 g, 71.6 percent).LC/MS (ES, m/z): [M+H]+ 152.0'H-NMR (300 MHz, CDC13): δ 6.68 - 6.74 (m, 2H), 6.43 - 6.48 (m, 1H), 3.27 - 3.31 (m, 2H), 2.74 - 2.79 (t, 7 = 6.6 Hz, 2H), 1.91 - 1.99(m, 2H)
Reference:
[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15656 - 15661[2] Angew. Chem., 2016, vol. 128, # 50, p. 15885 - 15890,6
[3] ACS Catalysis, 2018, vol. 8, # 5, p. 4545 - 4557
[4] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[5] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 753 - 760
[6] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 45
[7] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[8] Journal of Fluorine Chemistry, 2001, vol. 111, # 1, p. 1 - 10
[9] Patent: WO2009/87649, 2009, A1, . Location in patent: Page/Page column 24
[10] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 10
[11] Green Chemistry, 2017, vol. 19, # 3, p. 749 - 756
[12] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[13] Organic Letters, 2018, vol. 20, # 4, p. 1171 - 1174
[14] Molecular Catalysis, 2018, vol. 452, p. 145 - 153
[15] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9950 - 9954[16] Angew. Chem., 2018, vol. 130, p. 10098 - 10102,5
19
[ 396-30-5 ]
[ 86324-51-8 ]
Reference:
[1] Journal of Medicinal Chemistry, 1983, vol. 26, # 9, p. 1267 - 1277
With sodium cyanoborohydride; acetic acid; at 20℃; for 12h;
Sodium cyanoborohydride (6.45 g, 103 mmol ) was added gradually to the solution of 6-fluoro quinoline (5 g, 34 mmol) in glacial acetic acid (100 ml) at ambient temperature. After stirring for 12 h the reaction mixture was quenched in water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with water, brine and dried over sodium sulfate, filtered and evaporated in vacuo, the residue was purified by a silica gel column with 1 % to 5% ethyl acetate in petroleum ether to afford 6-fluoro- 1 , 2,3, 4-tetrahydroquinoline as a light yellow liquid (3.65 g, 71.6 %).LC/MS (ES, m/z): [M+H]+ 152.0'H-NMR (300 MHz, CDC13): delta 6.68 - 6.74 (m, 2H), 6.43 - 6.48 (m, 1H), 3.27 - 3.31 (m, 2H), 2.74 - 2.79 (t, 7 = 6.6 Hz, 2H), 1.91 - 1.99(m, 2H)
With sodium cyanoborohydride; In acetic acid; at 20℃; for 6h;
Sodium cyanoborohydride (3 eq) was added gradually to the solution of 6-fluoro quinoline (1 eq) in glacial acetic acid (3 v) at ambient temperature. After stirring for 6 h the reaction mixture was quenched in water and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over sodium sulfate, filtered and evaporated in vacuo to get crude product. The desired product was purified by column chromatography (SiO2, 3:7 hexane:EtOAc) afforded title compound as light yellow liquid.
With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; under 3102.97 Torr;
To a solution of 6-aminoquinoline (1.0 g) in 42% tetrafluoroboric acid (5 ml), sodium nitrite (527 mg) was added under ice cooling and stirred at the same temperature for 1 hour. After addition of diethyl ether:ethyl acetate = 1:1 (10 ml), the reaction mixture was decanted and the precipitate was dried. To the dried product, toluene (20 ml) was added and heated under reflux for 2 hours. The reaction mixture was decanted, and the resulting residue was dissolved in 1M aqueous hydrochloric acid and alkalized with saturated aqueous sodium carbonate. Insoluble materials were filtered off and the filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium 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 (eluting solvent: n-hexane:diethyl ether = 4:1 to 1:1) to give <strong>[396-30-5]6-fluoroquinoline</strong> (273 mg) as an orange-colored oil. To a solution of <strong>[396-30-5]6-fluoroquinoline</strong> thus obtained (273 mg) in methanol (50 ml), 10% palladium on activated carbon (50 mg) was added and stirred overnight under a hydrogen atmosphere (60 psi) at room temperature. After the reaction mixture was filtered, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate = 10:1 to 4:1) to give the titled compound, i.e., 6-fluoro-1,2,3,4-tetrahydroquinoline (172 mg) as a light-brown oil. 1H NMR (300 MHz, CHLOROFORM-D) delta 1.86-1.97 (m, 2 H), 2.74 (t, J=6.5 Hz, 2 H), 3.23-3.30 (m, 2 H), 3.69 (brs, 1 H), 6.35-6.45 (m, 1 H), 6.62-6.72 (m, 2 H).
With hydrogen; In methanol; at 80℃; under 750.075 Torr; for 4h;Autoclave;
General procedure: Typically, 1.0 mmol of quinoline compounds, 6 mL of solvent and acertain amount of PdCIL-T catalyst were added into a 50 mL PTFEreaction vessel or thick walled pressure vessel. The mixture was stirredfor 2 min to ensure complete dispersion of the catalyst and then placedin a 50 mL stainless-steel autoclave. After being flushed three timeswith H2, the pressure was elevated to 1-10 atm at room temperature.The autoclave was then heated to 30-120 C with a magnetic stir for acertain time. Subsequently, the catalyst was removed from the mixtureby centrifugation, and the liquid sample was analyzed by GC or GC-MS.The calculations of conversion and selectivity were based on the followingformula: Conversion=[consumed substrate]/[initial substrate]×100%, Selectivity=[py-THQs]/[all hydrogenated products]×100%.
With iodine; hydrazine; In methanol; chlorobenzene;
EXAMPLE 30 3-Fluoroimidazo[1,2-a: 3,4-a']diquinolin-15-ium Iodide STR36 A mixture of 294 g. of <strong>[396-30-5]6-fluoroquinoline</strong>, 74.6 g. of quinaldine, 1.7 l. of chlorobenzene and 254 g. of iodine is stirred for 2 hours at 20°-25° C., then stirred and heated at 100° C. for 4 days. About 1 l. of solvent is removed by evaporation at reduced pressure and the residue is cooled to 0°-5° C. The precipitate is collected, washed with cold chlorobenzene, dried and pulverized. The finely divided solid is suspended with stirring and cooling in 500 ml. of methanol and 55 ml. of hydrazine is added to destroy excess iodine. The resulting solid 3-fluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration, washed with cold methanol and dried; m.p. 310°-316° C. In a similar manner, from the appropriate quinoline and quinaldine, the following products are obtained:
With iodine; hydrazine hydrate; In methanol; chlorobenzene;
EXAMPLE 37 3,10-Difluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium Iodide. STR43 A mixture of 16.1 g. of 6-fluoroquinaldine, 58.9 g. of <strong>[396-30-5]6-fluoroquinoline</strong>, 70 ml. of chlorobenzene and 50.8 g. of iodine is stirred at 20°-25° C. for 1 hour, then heated at 95°-100° C. for 4 days. The precipitate is collected and suspended in 300 ml. of methanol. The methanol suspension is treated with 17 ml. of 85percent hydrazine hydrate and the resulting solid 3,10-difluoroimidazo[1,2-a:3,4-a']diquinolin-15-ium iodide is collected by filtration; m.p. >360° C., after crystallization from methanol.
Example 90 : 6-((RS)S- {3- [(6-fluoro-quinolin-5-ylmethyl)-amino] -propyl}-2-oxo- oxazolidin-3-yl)-4H-benzo [1 ,4] thiazin-3-one:; 90. i. <strong>[396-30-5]6-fluoro-quinoline</strong>-5-carbaldehyde:; To a solution of DIPA (1.1 mL, 7.75 mmol)) in TetaF (820 mL) cooled to -78°C, was added n-BuLi (2.57V in hexanes, 3 mL). The mixture was stirred 5 minutes at this temperature and was warmed in an ice-bath. After 10 min, the mixture was cooled down to -78°C and a solution of 3-fiuoro-6-methoxy-quinoline (see WO 2005/054232; 0.95 g, 6.46 mmol) in TetaF (8 + 2 mL rinse) was added. The reaction proceeded for 4 h. DMF (0.75 mL, 9.68 mmol) was added. The mixture was stirred 30 min at -78°C. The mixture was warmed to rt, stirred further 30 min and water (20 mL) was added. The two layers were decanted. The aq. layer was extracted with EA (2 x 50 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was chromatographed (etaept-EA 1-1) to afford first the starting material and then the expected aldehyde (0.17 g) as a 2-1 mixture with its regioisomer.1H NMR (CDC13) delta: 10.76 (s, 2/3 eta), 10.48 (s, 1/3 eta), 9.59 (m, 2/3 eta), 8.94 (m, 1 eta), 8.65 (d, J = 6.7 Hz, 1/3 H), 8.37 (ddd, J = 9.1, 5.3, 0.6 Hz, 2/3 H), 8.13 (m, 2/3 H), 7.50 (m, 5/3 H).
To a solution of DIPA (1.1 mL) in THF (20 mL) cooled to -78°C, was added /?-BuLi (2.5N in Hex, 3 mL). The mixture was stirred 5 min at this temperature and was warmed in an ice-bath. After 10 min, the mixture was cooled down to -78°C and treated with a solution of <strong>[396-30-5]6-fluoroquinoline</strong> (0.95 g; commercial) in THF (10 mL). After 4 h, DMF (0.75 mL) was added and the mixture was further stirred for 30 min. The mixture was warmed to rt, further stirred for 30 min and treated with water (20 mL). The two layers were decanted. The aq. layer was extracted with EA (2 x 50 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 1-1), affording the expected aldehydes in a 2:1 mixture favouring the isomer with the aldehyde at C-5 as a yellowish solid (0.17 g; 15percent yield).1H NMR (CDCl3) delta: 10.76 (s, 2/3 H, aldehyde at C-5); 10.47 (s, 1/3 H, aldehyde at C-6); 9.59 (m); 8.97 (m); 8.65 (d, J = 6.7 Hz); 8.37 (dd, J = 9.4, 5.6 Hz); 8.15 (m); 7.52 (m).
To a solution of DIPA (1.1 mL) in THF (20 mL) cooled to -78° C., was added n-BuLi (2.5N in Hex, 3 mL). The mixture was stirred 5 min at this temperature and was warmed in an ice-bath. After 10 min, the mixture was cooled down to -78° C. and treated with a solution of <strong>[396-30-5]6-fluoroquinoline</strong> (0.95 g; commercial) in THF (10 mL). After 4 h, DMF (0.75 mL) was added and the mixture was further stirred for 30 min. The mixture was warmed to rt, further stirred for 30 min and treated with water (20 mL). The two layers were decanted. The aq. layer was extracted with EA (2.x.50 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 1-1), affording the expected aldehydes in a 2:1 mixture favouring the isomer with the aldehyde at C-5 as a yellowish solid (0.17 g; 15percent yield).1H NMR (CDCl3) delta: 10.76 (s, 2/3 H, aldehyde at C-5); 10.47 (s, 1/3 H, aldehyde at C-6); 9.59 (m); 8.97 (m); 8.65 (d, J=6.7 Hz); 8.37 (dd, J=9.4, 5.6 Hz); 8.15 (m); 7.52 (m).
With Selectfluor; barium(II) oxide; silver(l) oxide; In acetone; at 23 - 90℃; for 2h;
To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (69.6 mg, 0.300 mmol, 3.00 equiv), barium oxide (17.2 mg, 0.110 mmol, 1.10 equiv), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial. The reaction mixture was cooled to 23 °C, passed through a pad of Celite and concentrated under reduced pressure. To the residue was added CH2Cl2 (20 mL) and a saturated aqueous solution of NaHCO3 (20 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on preparative TLC.
With diethylazodicarboxylate; In chloroform; toluene; at 20℃; for 12h;
General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1,2,3,4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wt% in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHCl3 (1.0 mL) was added. The reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with EtOAc:hexane (1:5) to give quinolines. In case of 2f and 2m, the product spot was close to the spot of the remained DEAD. To eliminate the remained DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred.[19] After 10 min, the reaction mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with CHCl3:hexane (1:1) to give quinolines.
68%
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen; In N,N-dimethyl-formamide; for 12h;
General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for 1H and 100 MHz for 13C, using CDCl3 as solvent with TMS as the internal standard. Thin-layer chromatography was performed on silica gel 60 F254 (Sinopharm) thin-layer chromatography plates using petroleum ether/ethyl acetate (10:1 v/v) as the mobile phase.
With oxygen; In 1,3,5-trimethyl-benzene; at 80℃; under 760.051 Torr; for 9.5h;
General procedure: 200mg Ni2Mn-LDH type hydrotalcite catalyst, 0.5mmol tetrahydroquinoline and 2mL 1,3,5-trimethylbenzene solvent Was added to the reactor, the reaction was carried out at atmospheric pressure and at a temperature of 80 C. The reaction time was 2.5 h under an atmosphere of oxygen, and the contents of the quinoline, the starting material, in the liquid were analyzed by gas chromatography internal standard method (nitrobenzene as internal standard) Content,The conversion and selectivity of the reaction were calculated. The conversion of tetrahydroquinoline was> 99% and the selectivity of the reaction was 78.3%
2-(6-fluoroquinolin-2-yl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With C10H3F6IO4; In ethyl acetate; at 60℃; for 8h;
General procedure: quinoline 1a (64.5 mg, 0.5 mmol), saccharin 2a (100.6 mg, 0.55 mmol) and PhI(OCOCF3)2 (430.0 mg, 1.0 mmol) were added to EtOAc2 (3 mL). The mixture was stirred at 60 oC for 8.0 h (monitored by TLC), quenched with water, extracted with dichloromethane (5×3 ml), and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by a shot flash silica gel column chromatography (EtOAc/petro ether = 1:6) to give compound 3a as a white solid (97.2 mg, 79percent).
With water; chloroacetic acid ethyl ester; In ethyl acetate; for 0.5h;Microwave irradiation;
In a 50mL pressure-resistant reaction tube, Adding 1.64 g of <strong>[396-30-5]6-fluoroquinoline</strong> in sequence, Ethyl chloroacetate 1.23g, Distilled water 0.54g, 20 ml of ethyl acetate, The resulting mixture was subjected to microwave irradiation for 30 minutes in a 300 W microwave stirring reaction apparatus. Washing the reaction solution with hot water, Liquid separation, Collect organic phase, Ethyl acetate and ethyl chloroacetate were removed under reduced pressure. Recrystallization to give the corresponding 6-fluoro-2-(1H)-quinolinone 1.50g, The yield was 92percent.