[ CAS No. 529-37-3 ]

Name: 529-37-3|Quinolin-4(1H)-one|95%
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Product Details of [ 529-37-3 ]

CAS No. :	529-37-3	MDL No. :	MFCD00006777
Formula :	C₉H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PMZDQRJGMBOQBF-UHFFFAOYSA-N
M.W :	145.16	Pubchem ID :	69141
Synonyms :

Safety of [ 529-37-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 529-37-3 ]

* 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 [ 529-37-3 ]
Downstream synthetic route of [ 529-37-3 ]

[ 529-37-3 ] Synthesis Path-Upstream 1~8

1
[ 529-37-3 ]
[ 41320-96-1 ]
[ 3964-04-3 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239
[2] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 50, p. 239

2
[ 91-22-5 ]
[ 148-24-3 ]
[ 578-67-6 ]
[ 10470-83-4 ]
[ 59-31-4 ]
[ 529-37-3 ]
[ 529-23-7 ]

Reference： [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658

3
[ 91-22-5 ]
[ 148-24-3 ]
[ 578-67-6 ]
[ 10470-83-4 ]
[ 59-31-4 ]
[ 529-37-3 ]
[ 529-23-7 ]

Reference： [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658

4
[ 529-37-3 ]
[ 74575-17-0 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 1831 - 1843
[2] Tetrahedron, 2013, vol. 69, # 45, p. 9512 - 9519

5
[ 529-37-3 ]
[ 40106-98-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 13, p. 3731 - 3742

6
[ 529-37-3 ]
[ 23833-99-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 13, p. 3731 - 3742

7
[ 529-37-3 ]
[ 7697-37-2 ]
[ 50332-66-6 ]

Reference： [1] Journal of the Chemical Society, 1949, p. 1367,1370

8
[ 529-37-3 ]
[ 611-36-9 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1982, vol. 324, # 3, p. 369 - 378

[ 529-37-3 ] Synthesis Path-Downstream 1~63

1
[ 4295-36-7 ]
[ 529-37-3 ]

Reference： [1]Australian Journal of Chemistry,2011,vol. 64,p. 454 - 470
[2]Journal of the Chemical Society,1950,p. 1485,1490

2
[ 492-27-3 ]
[ 529-37-3 ]

Reference： [1]Journal of the American Chemical Society,1944,vol. 66,p. 1166,1168
[2]Journal of the American Chemical Society,1946,vol. 68,p. 2685
[3]Monatshefte fur Chemie,1881,vol. 2,p. 68

3
[ 34785-11-0 ]
[ 529-37-3 ]

Reference： [1]Chemische Berichte,1901,vol. 34,p. 2709
Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie,1901,vol. 33,p. 402

4
[ 7377-75-5 ]
[ 529-37-3 ]

Yield	Reaction Conditions	Operation in experiment
97.9%	With polyphosphoric acid; at 100℃;	The compound 1 obtained in the previous step was mixed with 40 mL of polyphosphoric acid (PPA), and the reaction was stirred at 100 C for 1-2 hours. The end of the reaction was monitored by TLC. After the reaction was completed, the reaction solution was poured into 200 mL of ice water, and the pH was adjusted with sodium carbonate. = 5-6, extracted with 250 * 2 mL of ethyl acetate, combined organic layers, dried over anhydrous sodium sulfate, and concentrated the filtrate under reduced pressure to obtain a pale yellow solid compound 2 (14.22 g, 97.9%, HPLC: 98.65%);
14.22 g	With polyphosphoric acid; at 100℃;	The compound 1 obtained in the previous step was mixed with 40 mL of polyphosphoric acid (PPA), and the reaction was stirred at 100 C for 1-2 hours. The end of the reaction was monitored by TLC. After the reaction was completed, the reaction solution was poured into 200 mL of ice water and the pH was adjusted with sodium carbonate = 5-6, extracted with 250 * 2 mL of ethyl acetate, combined organic layers, dried over anhydrous sodium sulfate, and concentrated the filtrate under reduced pressure to obtain a pale yellow solid compound 2 (14.22 g, 97.9%, HPLC: 98.65%).

Reference： [1]Patent: CN110698396,2020,A .Location in patent: Paragraph 0054; 0055; 0056; 0059; 0060
[2]Patent: US2478125,1944,
[3]Patent: CN110804055,2020,A .Location in patent: Paragraph 0089-0091; 0094; 0095

5
[ 529-37-3 ]
[ 74-88-4 ]
[ 83-54-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1992,p. 351 - 356
[2]Chemistry - A European Journal,2015,vol. 21,p. 2339 - 2342
[3]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2445 - 2449
[4]European Journal of Inorganic Chemistry,2020,vol. 2020,p. 1011 - 1017
[5]Tetrahedron,2006,vol. 62,p. 10065 - 10071
[6]Monatshefte fur Chemie,1922,vol. 43,p. 474

6
[ 529-37-3 ]
[ 611-35-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3731 - 3742
[2]Molecules,2020,vol. 25
[3]Heterocycles,2006,vol. 68,p. 1973 - 1979
[4]Monatshefte fur Chemie,1881,vol. 2,p. 83
[5]Heterocycles,2012,vol. 86,p. 1583 - 1590

7
[ 529-37-3 ]
[ 41320-96-1 ]
[ 3964-04-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1894,vol. <2> 50,p. 239
[2]Journal fur praktische Chemie (Leipzig 1954),1894,vol. <2> 50,p. 239

8
[ 485-71-2 ]
[ 529-37-3 ]

Reference： [1]Monatshefte fur Chemie,vol. l0,p. 726

9
[ 529-37-3 ]
[ 100-39-0 ]
[ 24220-92-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 107 - 112
[2]Advanced Synthesis and Catalysis,2010,vol. 352,p. 2445 - 2449
[3]Chemistry - A European Journal,2015,vol. 21,p. 2339 - 2342
[4]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5719 - 5726
[5]Advanced Synthesis and Catalysis,2018,vol. 360,p. 379 - 384

10
[ 529-37-3 ]
[ 2524-04-1 ]
[ 3689-24-5 ]
[ 93516-19-9 ]

Reference： [1]Synthesis,1984,p. 491 - 493

11
[ 529-37-3 ]
[ 96-32-2 ]
[ 91538-63-5 ]

Yield	Reaction Conditions	Operation in experiment
2.82 g	With potassium carbonate In N,N-dimethyl-formamide for 21h; Ambient temperature;

Reference： [1]Hutt, Marland P.; MacKellar, Forrest A. [Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 349 - 352]

12
[ 529-37-3 ]
[ 624-83-9 ]
[ 83920-47-2 ]

Reference： [1]Tetrahedron Letters,1982,vol. 23,p. 3181 - 3184
[2]Synthesis,1983,p. 593 - 595
[3]Heterocycles,1983,vol. 20,p. 140
[4]Heterocycles,1984,vol. 21,p. 687

13
[ 529-37-3 ]
[ 79-22-1 ]
methyl 4(1H)-quinolone-1-carboxylate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 917 - 920
[2]European Journal of Inorganic Chemistry,2020,vol. 2020,p. 1011 - 1017

14
[ 529-37-3 ]
[ 3173-56-6 ]
[ 83920-50-7 ]

Reference： [1]Synthesis,1983,p. 593 - 595
[2]Tetrahedron Letters,1982,vol. 23,p. 3181 - 3184
[3]Heterocycles,1983,vol. 20,p. 140
[4]Heterocycles,1984,vol. 21,p. 687

15
[ 529-37-3 ]
[ 109-90-0 ]
[ 87722-73-4 ]

Reference： [1]Synthesis,1983,p. 593 - 595
[2]Heterocycles,1983,vol. 20,p. 140
[3]Heterocycles,1984,vol. 21,p. 687

16
[ 529-37-3 ]
[ 111-36-4 ]
[ 87722-74-5 ]

Reference： [1]Synthesis,1983,p. 593 - 595
[2]Heterocycles,1983,vol. 20,p. 140
[3]Heterocycles,1984,vol. 21,p. 687

17
[ 529-37-3 ]
[ 74-86-2 ]
[ 71314-94-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 2202 - 2204
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 2451 - 2454

18
[ 15568-92-0 ]
[ 529-37-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	In diphenylether; at 250℃; for 0.5h;Inert atmosphere;	Diphenylether (140 mL) was heated to 250 C and stirred vigorously under nitrogen atmosphere. 5-Anilinomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione (6) (26.30 g, 0.11 mol) was added portionwise at the same temperature, and the reaction mixture was stirred for 30 min. The resulting solution was allowed to cool to 70 C and diluted with n-hexane (200 mL). The precipitate was filtered off, washed with n-hexane, and dried in vacuo. The title compound was obtained as a brown solid (14.26 g, 92%), mp 200-202 C (lit., 28 mp 199-203 C); 1H NMR (DMSO-d6, 400 MHz) delta 11.72 (br s, 1H), 8.08 (dd, 1H, J=0.8, 8.0 Hz), 7.88 (d, 1H, J=7.2 Hz), 7.66-7.60 (m, 1H), 7.53 (d, 1H, J=8.4 Hz), 7.34-7.27 (m, 1H), 6.02 (d, 1H, J=7.6 Hz); 13C NMR (DMSO-d6, 400 MHz) delta 176.7, 139.8, 139.2, 131.5, 125.7, 124.8, 122.9, 118.1, 108.6; C9H7NO (145.16); LCMS (ESI+) m/z 146 [M+H]+. Anal. Calcd for C9H7NO (145.16) C, 74.47; H, 4.86; N, 9.65. Found: C, 74.19; H, 4.84; N, 9.68.
90%	at 80℃; for 2h;Ionic liquid; Inert atmosphere;	(b) Typical experimental procedure for the cyclization of 4a-e: Compound 4a-e (5 mmol) and [BMIM]BF4/OTf (3 mL) were taken in a round bottomed flask having provision to carry out the reaction under nitrogen atmosphere. The contents of the flask were stirred magnetically at 80 +/- 2 C. The progress of the reaction was monitored on a TLC plate in pet.ether-ethyl acetate (8:2). After completion of the reaction, the product was extracted with ethyl acetate (3 × 10 mL). The solvent was recovered under reduced pressure (5 mm of Hg). The pasty mass thus obtained was extracted with diethyl ether (3 × 10 mL), dried over anhydrous sodium sulphate and ether was distilled. The product so obtained was purified by crystallization with ethanol/column chromatography (Merck Silica gel 60-120 mesh) and eluting TLC product with pet.ether-ethylacetate (8:2).

Reference： [1]Tetrahedron,2013,vol. 69,p. 9512 - 9519
[2]Journal of the Chemical Society. Chemical communications,1983,p. 957 - 958
[3]Journal of the Chemical Society. Chemical communications,1983,p. 957 - 958
[4]Tetrahedron Letters,2012,vol. 53,p. 859 - 862
[5]Journal of Organic Chemistry,2015,vol. 80,p. 1632 - 1643
[6]Synlett,2007,p. 2205 - 2208
[7]Synthetic Communications,1985,vol. 15,p. 125 - 134
[8]Synlett,2009,p. 1847 - 1851

19
[ 578-68-7 ]
[ 7664-93-9 ]
[ 529-37-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1894,vol. <2> 50,p. 239

20
[ 529-37-3 ]
[ 103-71-9 ]
[ 30696-07-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	at 210℃;

Reference： [1]Katritzky; Huang; Voronkov [Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 1043 - 1045]

21
[ 529-37-3 ]
[ 23138-50-3 ]
4-(4-ethylanilino)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	at 210℃;

Reference： [1]Katritzky; Huang; Voronkov [Journal of Organic Chemistry, 2001, vol. 66, # 3, p. 1043 - 1045]

22
[ 87488-61-7 ]
[ 529-37-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With palladium 10% on activated carbon; cyclohexene; In ethanol; water; for 2h;Inert atmosphere; Reflux;	2. Synthesis of intermediate 056-4 The intermediate 056-2 (75.6 g, 34.5 mmol) was dissolved in 100 mL of anhydrous ethanol in a 250 mL three-necked flask at room temperature under a nitrogen atmosphere, followed by adding cyclohexene (the intermediate 056-3) (14.2 g, 172.9 mmol) and palladium on carbon containing water (18.7 g, 10% Pd) into the reaction system at room temperature. The reaction was heated to reflux for 2 h. After the reaction was completed, the mixture was cooled to room temperature and then filtered by suction. The filtrate was collected and concentrated to dryness. The residue was washed with 100 mL of the mixed solvent (EA/PE = 1: 2) once. The solid was filtered by suction, and the filter cake was dried to give 4.2 g of the intermediate 056-4 (84%) as a yellow solid. LCMS: 146.1.

Reference： [1]European Journal of Inorganic Chemistry,2020,vol. 2020,p. 1011 - 1017
[2]Tetrahedron Letters,2005,vol. 46,p. 735 - 737
[3]Patent: EP3216786,2017,A1 .Location in patent: Paragraph 0417-0418

23
[ 529-37-3 ]
[ 501-53-1 ]
[ 172538-83-9 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5317 - 5319
[2]European Journal of Inorganic Chemistry,2020,vol. 2020,p. 1011 - 1017
[3]Journal of Organic Chemistry,2015,vol. 80,p. 1632 - 1643

24
[ 529-37-3 ]
[ 40106-98-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3731 - 3742

25
[ 529-37-3 ]
[ 23833-99-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3731 - 3742

26
3-hydroxy-2-phenyl-2H [ No CAS ]
[ 529-37-3 ]
[ 7722-84-1 ]
[ 31588-18-8 ]

Yield	Reaction Conditions	Operation in experiment
17%	With sodium hydroxide; In methanol; water;	EXAMPLE 21 3-Hydroxy-2-phenyl-4H-1-benzopyridin-4-one To a solution of 0.23 g (0.96 mmol) 3-hydroxy-2-phenyl-2H, 3H, 4H-1-benzopyridin-4-one, 0.94 g NaOH (in 4 mL water) and 35 mL MeOH was added 15 mL of H2 O2 over ice bath. The yellow solution was then stirred at room temperature for 4 hours before the mixture was poured into 300 mL of water. The resulting mixture was extracted with CH2 Cl2 and the solvent was removed from the organic phase. The resulting residue was recrystallized form toluene which gave the desired product in 17% yield. MP: 260-262 C.

Reference： [1]Patent: US5552551,1996,A

27
[ 529-37-3 ]
[ 82121-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; In ethyl acetate;	A mixture of the 4(1H)-quinolone (41.1 g), 40% formaldehyde solution (60 ml), and 1 molar sodium hydroxide solution (360 ml) was allowed to stand for seventy two hours at 35 C. The reaction mixture was then neutralised with glacial acetic acid (21.6 g) and the solution extracted continuously with ethyl acetate (800 ml) for 6 hours. Three crops, shown by NMR and t.l.c. to be identical and the required product, 3-hydroxymethyl-4-(1H)-quinolone, were filtered off.

Reference： [1]Patent: US4390541,1983,A

28
[ 613-89-8 ]
[ 109-94-4 ]
[ 529-37-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride; sodium methylate; In 1,4-dioxane; chloroform; water;	Example 2 Process for Producing 4-Quinolone 2-Aminoacetophenone (7.0 g, 52 mmol) was added to and dissolved in 1,4-dioxane (100 ml). To the solution obtained was added sodium methoxide (8.4 g, 156 mmol), and the mixture was stirred at room temperature for 30 minutes. Ethyl formate (21 ml, 261 mmol) was then added, and the mixture was stirred at room temperature for an additional 125 minutes. After adding water (5 ml) to the reaction solution, and stirring for 10 minutes, 10% hydrochloric acid was added to the mixture for neutralization. The reaction solution was then concentrated under reduced pressure. The residue was suspended in chloroform (100 ml), collected by filtration, washed with chloroform (100 ml), and then purified by silica gel column chromatography to give 4.5 g of the desired compound (yield 60%). 1H-NMR (DMSO-d6, 400 MHz): delta 6.02 (d, J=7.6 Hz, 1H), 7.30 (m, 1H), 7.53 (d, J=8.1 Hz, 1H), 7.63 (m, 1H), 7.89 (dd, J=6.1 Hz, 7.3 Hz, 1H), 8.08 (dd, J=1.5 Hz, 8.1 Hz, 1H), 11.74 (brs, 1H). Mass Spectrometry (FD-MS, m/z): 145 (M30).

Reference： [1]Patent: US6187926,2001,B1

29
[ 529-37-3 ]
3-iodoquinolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a stirred solution of 1H-quinolin-4-one (7) (10.00 g, 68.89 mmol) in DMF (100 mL) N-iodosuccinimide (16.74 g, 74.40 mmol) was added portionwise at room temperature. The reaction mixture was stirred for 3 h. The solvent was evaporated and the residue was boiled in water (100 mL). The precipitate was filtered off, washed with water, and dried in vacuo. The title compound was obtained as a beige solid (16.92 g, 91%), mp 296-298 C (lit., 29 mp 296-299 C); 1H NMR (DMSO-d6, 400 MHz) delta 12.18 (br s, 1H), 8.50 (d, 1H, J=6.4), 8.11 (d, 1H, J=8.0 Hz), 7.72-7.65 (m, 1H), 7.59 (d, 1H, J=8.0 Hz), 7.42-7.35 (m, 1H); 13C NMR (DMSO-d6, 400 MHz) delta 172.9, 144.5, 139.3, 131.8, 125.3, 124.0, 122.3, 118.3, 80.5; C9H6INO (271.06); LCMS (ESI+) m/z 272 [M+H]+. Anal. Calcd for C9H6INO (271.06) C, 39.88; H, 2.23; N, 5.17. Found: C, 39.73; H, 2.22; N, 5.18.
		lH-Quinolin-4-one (2.90 g, 20 mmol, 1 equiv) in 5 mL of DMF was treated with 1.12 g of KOH (2 equiv) and 5.30 g of iodine (1.05 equiv) for 2 hours. The reaction was quenched by slow addition of saturated aqueous solution of Na2S2theta3. Filtration gave 3-iodo- lH-quinolin-4-one as an off-white solid.
1.33 g	With iodine; sodium carbonate; In methanol; at 20℃;	A mixture of 1.40 g 2-aminoacetophenone (5, 10.37 mmol) and 2.0 cm3 dimethylformamide dimethylacetal (DMFDMA,15.12 mmol) in 20 cm3 toluene was heated at 95 C for 3 h. The reaction was then cooled at room temperature. The excess of the solvent was evaporated under vacuum using rotavapor and the residue was recrystallized from EtOAc-hexane to give quinolin-4(1H)-one 6 as a yellow solid (1.24 g, 75%). To a solution of compound 6 in 20 cm3 MeOH, 2.05 g iodine (8.72 mmol) as solid and 0.92 g Na2CO3 (8.72 mmol) were added. The reaction mixture was allowed to stir overnight at room temperature. A solution of saturated aqueous sodium thiosulfate (10 cm3) was added and the mixture was extracted by CHCl3 (3 9 50 cm3). The organic solution was dried(Na2SO4), filtered and evaporated under reduced pressure.The resulting crude product was purified by column chromatography (silica gel, hexane:EtOAc, 1:1) to afford 3-iodoquinolin-4(1H)-one (6) as yellow solid (1.33 g,56%). M.p.: 216-218 C (Lit. [21] 217-218 C); the 1HNMR spectrum was identical to that given in [21].

Reference： [1]Tetrahedron,2013,vol. 69,p. 9512 - 9519
[2]Journal of Organic Chemistry,2015,vol. 80,p. 6649 - 6659
[3]Journal of Organic Chemistry,2015,vol. 80,p. 6649 - 6659
[4]Chemistry - A European Journal,2019,vol. 25,p. 3662 - 3674
[5]Synlett,2010,p. 462 - 466
[6]Patent: WO2007/59108,2007,A2 .Location in patent: Page/Page column 171
[7]Monatshefte fur Chemie,2018,vol. 149,p. 1857 - 1864

30
[ 529-37-3 ]
[ 74575-17-0 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843
[2]Tetrahedron,2013,vol. 69,p. 9512 - 9519

31
[ 529-37-3 ]
[ 68158-36-1 ]

Yield	Reaction Conditions	Operation in experiment
99%		The stirred solution of 1H-quinolin-4-one (7) (15.00 g, 0.10 mol) in acetic acid (90 mL) was refluxed for 10 min and bromine (16.51 g, 0.10 mol) was added dropwise at the same temperature. The reaction mixture was stirred for 2 h, then it was allowed to cool to room temperature. The resulting suspension was poured on crushed ice (340 mL) and diluted further with sodium thiosulfate solution (1 N, 50 mL). The resulting precipitate was filtered off, washed with water and dried in vacuo. The title compound was obtained as a beige solid (22.94 g, 99%), mp 199-201 C (lit., 30 mp 278-279 C); 1H NMR (DMSO-d6, 400 MHz) delta 12.27 (br s, 1H), 8.47 (d, 1H, J=6.4 Hz), 8.14 (dd, 1H, J=0.8, 8.0 Hz), 7.72-7.66 (m, 1H), 7.60 (d, 1H, J=8.0 Hz), 7.42-7.36 (m, 1H); 13C NMR (DMSO-d6, 400 MHz) delta 171.2, 140.0, 139.1, 131.8, 125.1, 124.1, 123.9, 118.4, 104.0; C9H6BrNO (224.06); LCMS (ESI+) m/z 224, 226 [M+H]+. Anal. Calcd for C9H6BrNO (224.06) C, 48.25; H, 2.70; N, 6.25. Found: C, 48.08; H, 2.69; N, 6.27.
91.3%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 80℃;	Compound 2 (10.00g, 68.87mmol, 1.00eq) and N-bromosuccinimide (14.71g, 82.64mmol, 1.20eq) were dissolved in 60mL DMF, and the reaction was stirred at 80 C for 3-5h. The reaction was monitored by TLC At the end of the reaction, after the reaction was completed, most of the DMF was removed by concentration under reduced pressure. The residue was added with 100 mL of water and extracted twice with 150 * 2 mL of ethyl acetate. The organic layers were combined, and the organic layer was washed once with 200 mL of saturated saline. After drying over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a yellow solid compound 3 (14.10 g, 91.3%, HPLC: 95.41%);
91.3%	In N,N-dimethyl-formamide; at 80℃;	Compound 2 (10.00g, 68.87mmol, 1.00eq) and N-bromosuccinimide (14.71g, 82.64mmol, 1.20eq) were dissolved in 60mL DMF, and the reaction was stirred at 80 C for 3-5h. The reaction was monitored by TLC At the end of the reaction, after the reaction was completed, most of the DMF was removed by concentration under reduced pressure. The residue was added with 100 mL of water and extracted twice with 150 * 2 mL of ethyl acetate. The organic layers were combined, and the organic layer was washed once with 200 mL of saturated saline. After drying over anhydrous sodium sulfate, the filtrate was concentrated under reduced pressure to obtain a yellow solid compound 3 (14.10 g, 91.3%, HPLC: 95.41%).

Reference： [1]Tetrahedron,2013,vol. 69,p. 9512 - 9519
[2]Patent: CN110698396,2020,A .Location in patent: Paragraph 0054; 0055; 0056; 0061; 0062
[3]Patent: CN110804055,2020,A .Location in patent: Paragraph 0089-0091; 0096; 0097
[4]Journal of Medicinal Chemistry,2012,vol. 55,p. 1831 - 1843

32
[ 529-37-3 ]
[ 66003-76-7 ]
[ 30696-04-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.

Reference： [1]Synlett,2016,vol. 27,p. 604 - 610
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4956 - 4961

33
di(4-chlorophenyl)iodonium trifluoromethanesulfonate [ No CAS ]
[ 529-37-3 ]
[ 76893-62-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.

Reference： [1]Synlett,2016,vol. 27,p. 604 - 610

34
[ 529-37-3 ]
[ 139139-80-3 ]
4-(mesityloxy)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.

Reference： [1]Synlett,2016,vol. 27,p. 604 - 610

35
bis(4-methoxyphenyl)iodonium 4-methylbenzenesulfonate [ No CAS ]
[ 529-37-3 ]
[ 76893-61-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.

Reference： [1]Synlett,2016,vol. 27,p. 604 - 610

36
[ 529-37-3 ]
[ 142342-33-4 ]
4-(4-t-butylphenoxy)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.

Reference： [1]Synlett,2016,vol. 27,p. 604 - 610

37
C₁₄H₁₄I⁽¹⁺⁾*C₇H₇O₃S^(1-) [ No CAS ]
[ 529-37-3 ]
[ 83842-47-1 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: To a mixture of quinolone(0.69 mmol), diaryliodonium salt (0.69 mmol) and potassium carbonate (285 mg, 2.07 mmol)was added DMF (2-3 drops) in a 10 mL sealed tube. The reaction contents were irradiated (100W power) in a CEM Discover MW reactor at 100 C for 5 min. After completion of the reaction(by TLC), the reaction mixture was cooled, quenched with ice-cold water (20 mL) and extractedwith dichloromethane (2 × 20 mL). The combined organic layer was dried over anhydrousNa2SO4 and concentrated in vaccuo. The crude product thus obtained was purified through asilica gel (100-200) column-chromatography to afford pure 4-aryloxyquinolines 8 in 55-80%yields.

Reference： [1]Synlett,2016,vol. 27,p. 604 - 610

38
[ 1201-93-0 ]
[ 529-37-3 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 1812 - 1815

39
(E)-N-(2-(3-(dimethylamino)acryloyl)phenyl)propionamide [ No CAS ]
[ 529-37-3 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 2418 - 2421

40
[ 529-37-3 ]
[ 66003-76-7 ]
[ 40695-01-0 ]