[ CAS No. 155370-03-9 ]

Name: 155370-03-9|2-(4-Fluorophenyl)-2,3-dihydro-4(1H)-quinolinone|97%
Brand: Ambeed
SKU: A248683
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Quality Control of [ 155370-03-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 155370-03-9 ]

Product Details of [ 155370-03-9 ]

CAS No. :	155370-03-9	MDL No. :	MFCD09999181
Formula :	C₁₅H₁₂FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HQCCOFMBOJBRQY-UHFFFAOYSA-N
M.W :	241.26 g/mol	Pubchem ID :	16748770
Synonyms :

Calculated chemistry of [ 155370-03-9 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.13
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	71.21
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	3.02
Log Po/w (WLOGP) :	3.09
Log Po/w (MLOGP) :	2.86
Log Po/w (SILICOS-IT) :	3.64
Consensus Log Po/w :	2.97

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.67
Solubility :	0.0521 mg/ml ; 0.000216 mol/l
Class :	Soluble
Log S (Ali) :	-3.3
Solubility :	0.122 mg/ml ; 0.000506 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.74
Solubility :	0.000439 mg/ml ; 0.00000182 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Safety of [ 155370-03-9 ]

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 [ 155370-03-9 ]

* 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 [ 155370-03-9 ]
Downstream synthetic route of [ 155370-03-9 ]

[ 155370-03-9 ] Synthesis Path-Upstream 1~8

1
[ 156492-25-0 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With K-10 clay In neat (no solvent) at 85℃; for 0.0833333 h; Microwave irradiation	General procedure: (2E)-1-(2-aminophenyl)-3-(2-fluorophenyl)prop-2-en-1-one (1), (2E)-1-(2-aminophenyl)-3-(3-fluorophenyl)prop-2-en-1-one (2), and (2E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (3) (0.02 mol each) were dissolved in chloroform and uniformly adsorbed on the surface of K-10 clay (15 g each) in a Pyrex round bottomed flask. The solvent was evaporated under vacuum, and then the adsorbed material was transferred to a Pyrextube (2 cm diameter, 30 mL) and inserted inside the Milestone microwave oven. The mixture was heated using axed power of 350 W for 5 min at 85° C. The reaction mixture was dissolved in AcOEt (2 15 mL) and filtered off. The extract was evaporated to leave a crude mixture, which was purified by column chromatography over silica (hexane{AcOEt, 5:1) to afford the pure corresponding products (4, 5, and 6) in 92percent, 90percent, and 96percent yields,respectively; the assigned structures for the known compounds 2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one(4), 2-(3-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (5), and 2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (6) were confirmed by their spectral properties (1 H, 13C/APT, 2D-COSY NMR, IR, and LC-MS/MS )and by comparison with literature data.

Reference： [1] Tetrahedron Letters, 2007, vol. 48, # 1, p. 13 - 15
[2] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 850 - 866
[3] South African Journal of Chemistry, 1994, vol. 47, # 1, p. 21 - 25
[4] RSC Advances, 2015, vol. 5, # 103, p. 85128 - 85138
[5] Tetrahedron Letters, 2006, vol. 47, # 16, p. 2725 - 2729
[6] Journal of Chemical Research, Miniprint, 1994, # 2, p. 367 - 382

2
[ 262606-35-9 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With zirconyl(IV) nitrate hydrate In ethanol; water at 50℃; for 3 h; Green chemistry	General procedure: A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH(2 mL), H2O (2 mL), and ZrO(NO3)2·nH2O (46 mg, 20 molpercent) washeated with stirring at 50 °C while the progress of the reactionwas monitored by TLC. The reaction was then quenched withH2O (5 mL), and the mixture was extracted with Et2O (3 × 10mL). The combined organic extracts were washed with brine (5mL) then dried (Na2SO4), filtered, and concentrated underreduced pressure. The crude product was purified by columnchromatography [silica gel, hexane–EtOAc (10:1)]. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry1)5b,6b,11Off-white solid; yield: 218 mg (98percent); mp 153–155 °C. IR (KBr):3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095,974, 861 cm–1. 1H NMR (600 MHz, CDCl3): δ = 7.83 (dd, J = 8.5,1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40–7.36 (m, 2 H), 7.35–7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H),4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J =16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). 13C NMR (150MHz, CDCl3): δ = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5,119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M+].

Reference： [1] Synthetic Communications, 2010, vol. 40, # 4, p. 476 - 481
[2] Synthetic Communications, 2010, vol. 40, # 9, p. 1391 - 1398
[3] Synlett, 2018, vol. 29, # 2, p. 235 - 237
[4] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 6, p. 2111 - 2122

3
[ 459-57-4 ]
[ 551-93-9 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With C₂₂H₄₈N₄O₁₂S₄⁽⁴⁺⁾*4HO₄S^(1-) In ethanol; water at 20℃; for 1.6 h; Irradiation; Reflux	1 mmol of p-fluorobenzaldehyde, 1 mmol of o-aminoacetophenone and 0.09 mmol of high acidity ionic liquid were separately added to a 50 ml one-necked flask with a condenser tube containing 8 ml of 95percent aqueous ethanol and stirred at room temperature. Heating and refluxing, ultrasonic irradiation under the reaction for 1.6h, TLC (thin plate chromatography) detection, the disappearance of raw materials, the end of the reaction cooled to room temperature to precipitate a large number of solid, put it into the ice bath to continue cooling the solid, the amount of solid is no longer increased The precipitated solid was allowed to stand, suction, and the residue was washed with absolute ethanol (3 ml x 3) and dried in vacuo at 75 ° C to give2- (4-fluoro) -phenyl-2,3-dihydro-4 (1H) -quinolinone,The purity was 99.0percent and the yield was 94percent by high performance liquid chromatography. The filtrate is directly added to the fluorobenzaldehyde, o-amino acetophenone after repeated use.
85%	With silver trifluoromethanesulfonate In methanol for 18 h; Reflux; Inert atmosphere	General procedure: AgOTf (26 mg, 10 molpercent) was added to a solution of an o-aminoacetophenone (1.0 mmol) and an aryl aldehyde (1.2 mmol) in MeOH (5mL) at r.t. The reaction mixture was stirred under reflux for 12–24 h. After the reaction was complete, as indicated by TLC, the excess solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexanes–EtOAc, 20:1) to yield the desired product.

Reference： [1] Patent: CN107162970, 2017, A, . Location in patent: Paragraph 0050; 0051; 0052
[2] Synthesis (Germany), 2015, vol. 47, # 24, p. 3881 - 3890
[3] Tetrahedron Letters, 2007, vol. 48, # 28, p. 4935 - 4937
[4] Tetrahedron Letters, 2016, vol. 57, # 49, p. 5442 - 5445

4
[ 1425928-63-7 ]
[ 155370-03-9 ]

Reference： [1] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 327 - 334

5
[ 551-93-9 ]
[ 155370-03-9 ]

Reference： [1] South African Journal of Chemistry, 1994, vol. 47, # 1, p. 21 - 25
[2] Journal of Chemical Research, Miniprint, 1994, # 2, p. 367 - 382
[3] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 7 - 16
[4] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 327 - 334
[5] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 850 - 866

6
[ 459-57-4 ]
[ 155370-03-9 ]

Reference： [1] Journal of Chemical Research, Miniprint, 1994, # 2, p. 367 - 382
[2] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 850 - 866

7
[ 5234-26-4 ]
[ 155370-03-9 ]

Reference： [1] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 7 - 16
[2] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 327 - 334

8
[ 118-92-3 ]
[ 155370-03-9 ]

Reference： [1] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 7 - 16

[ 155370-03-9 ] Synthesis Path-Downstream 1~41

1
[ 156492-25-0 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With K-10 clay; In neat (no solvent); at 85℃; for 0.08333330000000001h;Microwave irradiation;	General procedure: (2E)-1-(2-aminophenyl)-3-(2-fluorophenyl)prop-2-en-1-one (1), (2E)-1-(2-aminophenyl)-3-(3-fluorophenyl)prop-2-en-1-one (2), and (2E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (3) (0.02 mol each) were dissolved in chloroform and uniformly adsorbed on the surface of K-10 clay (15 g each) in a Pyrex round bottomed flask. The solvent was evaporated under vacuum, and then the adsorbed material was transferred to a Pyrextube (2 cm diameter, 30 mL) and inserted inside the Milestone microwave oven. The mixture was heated using axed power of 350 W for 5 min at 85 C. The reaction mixture was dissolved in AcOEt (2 15 mL) and filtered off. The extract was evaporated to leave a crude mixture, which was purified by column chromatography over silica (hexane{AcOEt, 5:1) to afford the pure corresponding products (4, 5, and 6) in 92%, 90%, and 96% yields,respectively; the assigned structures for the known compounds 2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one(4), 2-(3-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (5), and 2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (6) were confirmed by their spectral properties (1 H, 13C/APT, 2D-COSY NMR, IR, and LC-MS/MS )and by comparison with literature data.

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 13 - 15
[2]Turkish Journal of Chemistry,2015,vol. 39,p. 850 - 866
[3]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25
[4]RSC Advances,2015,vol. 5,p. 85128 - 85138
[5]Tetrahedron Letters,2006,vol. 47,p. 2725 - 2729
[6]Journal of Chemical Research, Miniprint,1994,p. 367 - 382

2
[ 155370-03-9 ]
[ 155370-04-0 ]
5-(4-Fluoro-phenyl)-5,6-dihydro-4H-1,2,3,3a,6-pentaaza-benzo[e]azulene [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1994,p. 367 - 382

3
[ 155370-03-9 ]
[ 155370-04-0 ]

Reference： [1]Journal of Chemical Research, Miniprint,1995,p. 2319 - 2336

4
[ 67-56-1 ]
[ 155370-03-9 ]
2-(4'-fluorophenyl)-4-methoxyquinoline [ No CAS ]

Reference： [1]Journal of Chemical Research - Part S,1999,p. 706 - 707

5
[ 459-57-4 ]
[ 551-93-9 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With C22H48N4O12S4(4+)*4HO4S(1-); In ethanol; water; at 20℃; for 1.6h;Irradiation; Reflux;	1 mmol of p-fluorobenzaldehyde, 1 mmol of o-aminoacetophenone and 0.09 mmol of high acidity ionic liquid were separately added to a 50 ml one-necked flask with a condenser tube containing 8 ml of 95% aqueous ethanol and stirred at room temperature. Heating and refluxing, ultrasonic irradiation under the reaction for 1.6h, TLC (thin plate chromatography) detection, the disappearance of raw materials, the end of the reaction cooled to room temperature to precipitate a large number of solid, put it into the ice bath to continue cooling the solid, the amount of solid is no longer increased The precipitated solid was allowed to stand, suction, and the residue was washed with absolute ethanol (3 ml x 3) and dried in vacuo at 75 C to give2- (4-fluoro) -phenyl-2,3-dihydro-4 (1H) -quinolinone,The purity was 99.0% and the yield was 94% by high performance liquid chromatography. The filtrate is directly added to the fluorobenzaldehyde, o-amino acetophenone after repeated use.
85%	With silver trifluoromethanesulfonate; In methanol; for 18.0h;Reflux; Inert atmosphere;	General procedure: AgOTf (26 mg, 10 mol%) was added to a solution of an o-aminoacetophenone (1.0 mmol) and an aryl aldehyde (1.2 mmol) in MeOH (5mL) at r.t. The reaction mixture was stirred under reflux for 12-24 h. After the reaction was complete, as indicated by TLC, the excess solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexanes-EtOAc, 20:1) to yield the desired product.

Reference： [1]Patent: CN107162970,2017,A .Location in patent: Paragraph 0050; 0051; 0052
[2]Applied Organometallic Chemistry,2019,vol. 33
[3]Synthesis,2015,vol. 47,p. 3881 - 3890
[4]Tetrahedron Letters,2007,vol. 48,p. 4935 - 4937
[5]Tetrahedron Letters,2016,vol. 57,p. 5442 - 5445

6
[ 459-57-4 ]
PhCH₂CH₂MgHal [ No CAS ]
[ 155370-03-9 ]

Reference： [1]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25

7
[ 551-93-9 ]
[ 155370-03-9 ]

Reference： [1]South African Journal of Chemistry,1994,vol. 47,p. 21 - 25
[2]Journal of Chemical Research, Miniprint,1994,p. 367 - 382
[3]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16
[4]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334
[5]Turkish Journal of Chemistry,2015,vol. 39,p. 850 - 866

8
[ 459-57-4 ]
[ 155370-03-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1994,p. 367 - 382
[2]Turkish Journal of Chemistry,2015,vol. 39,p. 850 - 866

9
[ 872-85-5 ]
[ 155370-03-9 ]
[ 1171953-14-2 ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium hydroxide; In ethanol; water; at 20℃; for 24.0h;	An aqueous sodium hydroxide solution (6N, 2 mL) is added to a solution 2-(4-fluorophenyl)-2, 3- dihydroquinolin-4 (lH)-one (241 mg, lmmol) in ethanol (5mL). Pyridine -4- carboxaldehyde (126 mg, 1.2 mmol) is then added to the reaction mixture, which is stirred at room temperature for 24 hours.Subsequently, it is evaporated under reduced pressure. The residue is dissolved into chloroform and the organic layer is washed with water, dried over Na2SO4 and evaporated to dryness. Crude product further purified by column chromatography on silica gel using ethyl acetateracetone (97:03v/v) as eluent. Yield120 mg (36%); mp 144-1460C; 1HNMR (DMSO-d6) delta: 3.70 (s, 2H, CH2), 6.96 (d, 2H, H-2"and H-6"), 7.30-7.69 (m, 7H, H-6, H-7, H-8, H-2 H-3', H-5' and H-6'), 8.12 (d, IH, H-5), 8.30 (d, 2H, H-3" andH-5"), 11.81 (s, IH, NH); MS m/z 331 (MfH)+.

Reference： [1]Patent: WO2009/87684,2009,A2 .Location in patent: Page/Page column 31

10
[ 262606-35-9 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With zirconyl(IV) nitrate hydrate; In ethanol; water; at 50℃; for 3.0h;Green chemistry;	General procedure: A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH(2 mL), H2O (2 mL), and ZrO(NO3)2·nH2O (46 mg, 20 mol%) washeated with stirring at 50 C while the progress of the reactionwas monitored by TLC. The reaction was then quenched withH2O (5 mL), and the mixture was extracted with Et2O (3 × 10mL). The combined organic extracts were washed with brine (5mL) then dried (Na2SO4), filtered, and concentrated underreduced pressure. The crude product was purified by columnchromatography [silica gel, hexane-EtOAc (10:1)]. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry1)5b,6b,11Off-white solid; yield: 218 mg (98%); mp 153-155 C. IR (KBr):3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095,974, 861 cm-1. 1H NMR (600 MHz, CDCl3): delta = 7.83 (dd, J = 8.5,1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40-7.36 (m, 2 H), 7.35-7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H),4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J =16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). 13C NMR (150MHz, CDCl3): delta = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5,119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M+].

Reference： [1]Synthetic Communications,2010,vol. 40,p. 476 - 481
[2]Synthetic Communications,2010,vol. 40,p. 1391 - 1398
[3]Synlett,2018,vol. 29,p. 235 - 237
[4]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 2111 - 2122

11
[ 108-24-7 ]
[ 155370-03-9 ]
[ 1203590-61-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 18250 - 18251

12
[ 155370-03-9 ]
[ 1332337-52-6 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

13
[ 155370-03-9 ]
[ 1332337-56-0 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

14
[ 155370-03-9 ]
[ 1332337-60-6 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

15
[ 155370-03-9 ]
[ 1332337-64-0 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

16
[ 155370-03-9 ]
[ 1320360-56-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-Bromosuccinimide; In tetrachloromethane; chloroform; at 20℃; for 3.0h;	General procedure: NBS (1.00 g, 5.61 mmol) was added to a stirred suspension of 1a (0.50 g, 2.24 mmol) in carbon tetrachloride-chloroform (3:2, v/v; 40 mL). The mixture was stirred at room temperature for 3 h and then quenched with an ice-cold saturated solution of NaHCO3. The organic layer was separated and the aqueous phase was extracted twice with chloroform. The combined organic phases were washed with water and dried over MgSO4. The salt was filtered off and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel to afford 2a as a yellow solid (0.86 g, 70%).

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

17
[ 155370-03-9 ]
[ 1332337-68-4 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

18
[ 155370-03-9 ]
[ 1332337-72-0 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 6819 - 6825

19
C₁₇H₁₄FNO₂ [ No CAS ]
[ 155370-03-9 ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16

20
[ 118-92-3 ]
[ 155370-03-9 ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16

21
[ 5234-26-4 ]
[ 155370-03-9 ]

Reference： [1]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16
[2]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334

22
[ 155370-03-9 ]
[ 313822-47-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iodine; In dimethyl sulfoxide; at 80℃; for 12.0h;	General procedure: A mixture of 2 (1 mmol) and iodine (1.5 mmol) inDMSO was warmed at 80C in an oil bath for 12 hours. On completion of the reaction, the reaction mixture was poured onto saturated solution of sodium thiosulfate. The precipitated solid was collected and the desired product was purified by column chromatography using silica gel (60x120 mesh) with increasing percentage of ethyl acetate in hexaneas eluting solvent. The physical data of compounds are provided below.

Reference： [1]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334
[2]Archiv der Pharmazie,2013,vol. 346,p. 7 - 16

23
[ 1425928-63-7 ]
[ 155370-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; for 12.0h;Reflux;	General procedure: A mixture of 1 (1 mmol) and 5% HCl (10 ml) was refluxed for 12 hours. The reaction mixture was kept at room temperature and then basified with NH4OH. The precipitated solid was filtered sand recrystallized from ethanol. The physical data for the characterstic compound is shown below

Reference： [1]Letters in drug design and discovery,2013,vol. 10,p. 327 - 334

24
[ 110-53-2 ]
[ 155370-03-9 ]
C₂₀H₂₀FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		General procedure: To a solution of 2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (4), 2-(3-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (5), and <strong>[155370-03-9]2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one</strong> (6) (2.41 g, 0.01 mol for each) in DMF (10mL each) was added KOH (1.12 g, 0.02 mol each) and the resulting mixture was stirred at room temperature for 1 h. Then alkyl bromide (0.03 mol each) was added dropwise, and the reaction mixture was stirred overnight at room temperature. Then the reaction mixture was poured into 20 mL of water. The resulting mixture was extracted with CH2Cl2 (2 x 20 mL). The combined organic layer was washed with brine, dried over Na2SO4 , filtered, and concentrated in a vacuum to give crude products 7a-k, 8a-k, and 9a-k, which were purified by column chromatography using a mixture of n-hexane-chloroform (8.5:0.5) as eluent (yields are in Tables 1, 4, and 7).