70049-46-6|2,4-Dichloro-6-methoxyquinoline| Ambeed

CAS No. :	70049-46-6
Formula :	C₁₀H₇Cl₂NO
M.W :	228.08
SMILES Code :	COC1=CC=C2N=C(Cl)C=C(Cl)C2=C1
MDL No. :	MFCD03285967
InChI Key :	FUAYQQYYACASFP-UHFFFAOYSA-N
Pubchem ID :	948356

Safety of [ 70049-46-6 ]

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

Computational Chemistry of [ 70049-46-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	58.26
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.63
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.75
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.55
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.6
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.68
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.08
Solubility	0.019 mg/ml ; 0.0000833 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.91
Solubility	0.0282 mg/ml ; 0.000124 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.07
Solubility	0.00195 mg/ml ; 0.00000855 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.03 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.66

Application In Synthesis of [ 70049-46-6 ]

* 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 [ 70049-46-6 ]

[ 70049-46-6 ] Synthesis Path-Downstream 1~49

1
[ 151772-24-6 ]
[ 70049-46-6 ]

References: [1]Synthesis,1993,p. 623 - 626.
[2]Synthesis,1993,p. 623 - 626.

2
2,4-Dichloro-6-methoxy-quinoline-3-carboxylic acid [ No CAS ]
[ 70049-46-6 ]

References: [1]Synthesis,1993,p. 623 - 626.

3
[ 141-82-2 ]
[ 104-94-9 ]
[ 70049-46-6 ]

Yield	Reaction Conditions	Operation in experiment
35%	With trichlorophosphate; at 20℃; for 5.25h;Reflux;	2,4-DICHLORO-6-METHOXYQUINOLINE. Phosphorus(V)oxychloride (40 mL, 1.5 M) was added through a condenser into a 3-neck round bottom flask containing malonic acid (6.244 g, 60.00 mmol) and a stir bar at room temperature. While stirring, p-anisidine (9.236 g, 75.00 mmol) was added in small portions over a period of 15 minutes through an open neck of the round bottom flask. The reaction mixture was heated and stirred at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature before it was poured over crushed ice (700 mL). The pH of the resulting aqueous solution was then adjusted to 10 with concentrated ammonium hydroxide (85 mL). The aqueous suspension was extracted with dichloromethane. The combined organic layers were then dried over MgSO4 before concentration. Purification by column chromatography (0-5percent ethyl acetate in hexanes) yielded the title compound as a slightly yellow solid (4.7812 g, 35percent). Mp 170.5-171.5° C.; Rf=0.27 (2percent EtOAc/hexanes); IR (film) 3084, 3013, 2982, 1623, 1562, 1499 cm-1; 1H NMR (500 MHz, CDCl3) delta 7.90 (d, J=9.0 Hz, 1H), 7.45 (s, 1H), 7.40 (dd, J=9.0, 3.0 Hz, 1H), 7.36 (d, J=3.0 Hz, 1H), 3.96 (s, 3H); 13C NMR (125 MHz, CDCl3) ppm 158.9, 147.0, 144.0, 142.6, 130.4 126.3, 124.1, 122.0, 101.9, 55.7; HRMS submitted.
19%		A mixture of p- anisidine (100 g, 0.813 mol), and malonic acid (85.0 g, 0.817 mol) in POCI3 (500 mL) was refluxed for 6 hours. The excess POCI3 was removed in vacuo and the residue was neutralized with 8 M NaOH to pH 7. The aqueous layer was extracted with CH2CI2 (300 mL x 3), washed with brine (500 mL), dried over Na2S04 and concentrated under reduced pressure. Purification by column chromatography on silica gel (PE / EtOAc = 15/1) gave desired (35.0 g, yield: 19percent).
	With trichlorophosphate; at 20 - 105℃; for 3.25h;	POC13 (80 ml) was added through a condenser into a 250 mL round bottom flask containing malonic acid (25.3 g, 244 mmol) at 20 °C. While stirring, 4-methoxyaniline (20 g, 162 mmol) was added in small portions over a period of 15 minutes. The reaction mixture was heated and stirred at 105 °C for 3 h. Thenthe reaction mixture was cooled to 20 °C and concentrated in vacuo to remove POC13. The resulting residue was dissolved in DCM (200 mL). Then the mixture was poured into concentrated ammonium hydroxide and the final pH of the aquesous layer was about 10. The aqueous layer was extracted with DCM (3 x 100 mL). The combined organic layers were dried over Na2504, filtered and concentrated in vacuo. The resulting residue was purified by columnchromatography (5i02, PE:EtOAc =100:1 to 10:1) to give the title compound.

References: [1]Heterocyclic Communications,2001,vol. 7,p. 353 - 358.
[2]Research on Chemical Intermediates,2014,vol. 40,p. 1851 - 1866.
[3]Patent: US2012/88915,2012,A1 .Location in patent: Page/Page column 14.
[4]Chemistry of Heterocyclic Compounds,2015,vol. 51,p. 250 - 258.
Khim. Geterotsikl. Soedin.,2015,vol. 51,p. 250 - 258,9.
[5]Patent: WO2012/83165,2012,A1 .Location in patent: Page/Page column 95.
[6]Research on Chemical Intermediates,2013,vol. 39,p. 1807 - 1815.
[7]Molecules,2015,vol. 20,p. 7620 - 7636.
[8]Patent: WO2017/155765,2017,A1 .Location in patent: Page/Page column 68.

4
[ 68-12-2 ]
[ 70049-46-6 ]
[ 151772-24-6 ]

References: [1]Heterocyclic Communications,2001,vol. 7,p. 353 - 358.

6
[ 70049-46-6 ]
[ 419566-57-7 ]

References: [1]Heterocyclic Communications,2001,vol. 7,p. 353 - 358.

7
[ 70049-46-6 ]
[ 419566-62-4 ]

References: [1]Heterocyclic Communications,2001,vol. 7,p. 353 - 358.

8
[ 70049-46-6 ]
2-methoxy-8,9,10,11-tetrahydro-5H-dibenzo[b,h][1,6]naphthyridin-6-one [ No CAS ]

References: [1]Heterocyclic Communications,2001,vol. 7,p. 353 - 358.

9
[ 110-91-8 ]
[ 70049-46-6 ]
[ 952443-70-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In ethylene glycol; at 145℃; for 1.25h;Microwave reaction;	(1) A mixture of <strong>[70049-46-6]2,4-dichloro-<strong>[70049-46-6]6-methoxyquinoline</strong></strong> (0.228 g), morpholine (262 muL), N,N-diisopropylethylamine (348 muL), and ethylene glycol (4 mL) was heated with microwave (145°C) for 75 min with stirring. The reaction mixture was cooled to room temperature, followed by addition of water, the mixture was extracted with chloroform and washed with saturated brine, and the organic layer was dried with anhydrous sodium sulfate. The desiccant was removed by filtration, the residue concentrated under reduced pressure was purified by silica gel column chromatography (chloroform/hexane = 1/1) to obtain 2-chloro-6-methoxy-4-morpholinoquinoline (0.182 g).

References: [1]Patent: EP2003131,2008,A1 .Location in patent: Page/Page column 44.

10
[ 67-56-1 ]
[ 124-41-4 ]
[ 70049-46-6 ]
[ 952435-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	at 70℃; for 3h;	Reference Example 10: Synthesis of 2-chloro-4,6-dimethoxyquinoline To a solution of <strong>[70049-46-6]2,4-dichloro-<strong>[70049-46-6]6-methoxyquinoline</strong></strong> (0.97 g) synthesised from p-anisidine and malonic acid according to the method of in methanol (20 mL) was added sodium methoxide (1.37 g), and the mixture was stirred at 70°C for 3 h. The reaction solution was added dropwise to ice water, and the resulting solids were collected by filtration. The resulting solids were purified by silica gel column chromatography (hexane/ethyl acetate = 5:1) to obtain 2-chloro-4,6-dimethoxyquinoline (0.61 g) as white solids. LC/MS: ESI+ (m/z) 224 (M++1) 1H-NMR (300 MHz, CDCl3): delta7.83 (d, J=9.0 Hz, 1H),7.36 (d, J=2.7 Hz, 1H), 7.33 (dd, J=2.7 Hz, J=9.0 Hz, 1H), 4.04 (s, 3H), 3.91 (s, 3H) The following compounds were synthesised by the same method.

References: [1]Patent: EP2003131,2008,A1 .Location in patent: Page/Page column 63.

11
[ 20439-47-8 ]
[ 70049-46-6 ]
[ 1353892-00-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium t-butanolate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0); In alpha,alpha,alpha-trifluorotoluene; at 120℃; for 0.166667h;Microwave irradiation;	H,4CL6MEOQUIN-BAM. A 2-5 mL muW vial was charged with (R,R)-diaminocyclohexane (125.2 mg, 1.096 mmol), <strong>[70049-46-6]2,4-dichloro-<strong>[70049-46-6]6-methoxyquinoline</strong></strong> (500 mg, 2.190 mmol), Pd(dba)2 (12.6 mg, 22.0 mumol), rac-BINAP (13.6 mg, 22.0 mumol), and sodium tert-butoxide (316.2 mg, 3.290 mmol). See Wagaw et al., 1997, which is incorporated herein by reference. Trifluoromethylbenzene (3.8 mL) was added and the resulting suspension was heated at 120° C. and stirred in the microwave for 10 min. The reaction mixture was triturated with CH2Cl2 and filtered. The filtrate was concentrated and purified by column chromatography (10-20percent ethyl acetate in hexanes) to provide a yellow solid (420.3 mg, 77percent) that was pure by 1H NMR; [alpha]D20 +610 (c 0.18, CHCl3); Rf=0.18 (20percent EtOAc/hexanes); IR (film) 3218, 2925, 1605, 1495 cm-1; 1H NMR (600 MHz, CDCl3, 325 K) delta 7.64 (d, J=9.0 Hz, 2H), 7.30 (d, J=3.0 Hz, 2H), 7.25 (dd, J=9.0, 3.0 Hz, 2H), 6.38 (br s, 2H), 5.72 (br s, 2H), 4.05-3.90 (m, 2H), 3.91 (s, 6H), 2.39-2.25 (m, 2H), 1.90-1.80 (m, 2H), 1.55-1.35 (m, 4H); 13C NMR (150 MHz, CDCl3, 325 K) ppm 155.5, 155.4, 144.0, 141.4, 127.6, 121.9, 121.8, 111.8, 103.7, 56.1, 55.6, 33.0, 24.9; HRMS (ESI): Exact mass calcd for C26H27Cl2N4O2 [M+H]+ 497.1511. found 497.1500.

References: [1]Patent: US2012/88915,2012,A1 .Location in patent: Page/Page column 14-15.

12
[ 70049-46-6 ]
[ 1353891-43-6 ]

References: [1]Patent: US2012/88915,2012,A1 .

13
[ 141-82-2 ]
[ 90-04-0 ]
[ 70049-46-6 ]

Yield	Reaction Conditions	Operation in experiment
19%		A mixture of p- anisidine (100 g, 0.813 mol), and malonic acid (85.0 g, 0.817 mol) in POCl3 (500 mL) was refluxed for 6 hours. The excess POCl3 was removed in vacuo and the residue was neutralized with 8 M NaOH to pH 7. The aqueous layer was extracted with CH2CI2 (300 mL x 3), washed with brine (500 mL), dried over Na2S04 and concentrated in vacuo.Purification by column chromatography on silica gel (PE / EtOAc = 15/1) gave the desired product (35.0 g, yield: 19percent).

References: [1]Patent: WO2012/48181,2012,A1 .Location in patent: Page/Page column 78.

14
[ 70049-46-6 ]
[ 1371588-86-1 ]

References: [1]Patent: WO2012/48181,2012,A1 .

15
[ 70049-46-6 ]
[ 1371588-03-2 ]

References: [1]Patent: WO2012/48181,2012,A1 .

16
[ 70049-46-6 ]
[ 1371588-93-0 ]

References: [1]Patent: WO2012/48181,2012,A1 .

17
[ 70049-46-6 ]
[ 1371588-06-5 ]

References: [1]Patent: WO2012/48181,2012,A1 .

18
[ 70049-46-6 ]
[ 1371589-25-1 ]

References: [1]Patent: WO2012/48181,2012,A1 .
[2]Patent: WO2012/83165,2012,A1 .

19
[ 70049-46-6 ]
[ 1371589-24-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With ammonia; In methanol; at 150℃; for 16h;sealed tube;	A suspension of 2,4-dichloro-6- methoxyquinoline (5.00 g, 22.0 mmol) in NH3 (g) / MeOH (saturated, 40 mL) was heated to 150 °C for 16 hours in a sealed tube. The solvent was removed in vacuo and the residue was diluted with MeOH (20 mL). The mixture was filtered off and the filtrate was concentrated to give the crude product, which was purified by column chromatography on silica gel (PE / EtOAc = 2/1) to give 2-chloro-6-methoxyquinolin-4-amine (7.50 g, yield: 55percent) as a yellow solid.
55%	With ammonia; In methanol; at 150℃; for 16h;sealed tube;	A suspension of <strong>[70049-46-6]2,4-dichloro-<strong>[70049-46-6]6-methoxyquinoline</strong></strong> (5.00 g, 22.0 mmol) in NH3 (g) / MeOH (saturated, 40 mL) was heated to 150 °C for 16 hours in a sealed tube. The solvent was removed and the residue was diluted with MeOH (20 mL). The mixture was filtered off and the filtrate was concentrated to give the crude product. Purification by column chromatography on silica gel (PE / EtOAc = 2/1) gave product (7.50 g, yield: 55percent) as a solid

References: [1]Patent: WO2012/48181,2012,A1 .Location in patent: Page/Page column 79.
[2]Patent: WO2012/83165,2012,A1 .Location in patent: Page/Page column 95.
[3]Journal of Photochemistry and Photobiology A: Chemistry,2017,vol. 332,p. 72 - 86.

20
[ 70049-46-6 ]
[ 294653-58-0 ]
[ 1386328-64-8 ]

References: [1]Research on Chemical Intermediates,2013,vol. 39,p. 1807 - 1815.

21
[ 80-05-7 ]
[ 70049-46-6 ]
[ 1417625-38-7 ]

References: [1]Research on Chemical Intermediates,2013,vol. 39,p. 4259 - 4267.

22
[ 124-41-4 ]
[ 70049-46-6 ]
[ 952435-01-7 ]

References: [1]Research on Chemical Intermediates,2013,vol. 39,p. 4259 - 4267.

23
[ 70049-46-6 ]
[ 156304-06-2 ]
[ 1424371-19-6 ]

References: [1]Research on Chemical Intermediates,2014,vol. 40,p. 1851 - 1866.

24
[ 14300-45-9 ]
[ 70049-46-6 ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.
[2]Bioorganic Chemistry,2019,vol. 90.

25
[ 70049-46-6 ]
[ 878380-77-9 ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.

26
[ 70049-46-6 ]
6-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonitrile [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.
[2]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.
[3]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.

27
[ 70049-46-6 ]
[ 1029773-70-3 ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.
[2]Bioorganic Chemistry,2019,vol. 90.

28
[ 70049-46-6 ]
6-methoxy-4-[(4-methylphenyl)sulfonyl]quinolin-2(1H)-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.

29
[ 70049-46-6 ]
6-methoxy-2-oxo-1,2-dihydroquinoline-4-carbonitrile [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.
[2]Journal of Heterocyclic Chemistry,2014,vol. 51,p. E263-E275.

30
[ 70049-46-6 ]
[ 1276644-83-7 ]

31
[ 70049-46-6 ]
6-methoxy-2-(4-methyl-1,4-diazepan-1-yl)-N-(1-methylpiperidin-4-yl)quinolin-4-amine [ No CAS ]

References: [1]Molecules,2015,vol. 20,p. 7620 - 7636.

32
[ 41838-46-4 ]
[ 70049-46-6 ]
C₁₆H₂₀ClN₃O [ No CAS ]

References: [1]Molecules,2015,vol. 20,p. 7620 - 7636.

33
4-(3-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid ethyl ester [ No CAS ]
[ 70049-46-6 ]
ethyl 4-(3-(2-chloro-6-methoxyquinolin-4-yloxy)phenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃;	General procedure: A mixture of substituted 2,4-dichloroquinolines 2a-j (1mol), powdered K2CO3 (1.2 mol) and 4-(3-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate(1; 1 mol) in DMF was stirred at 70 °C for 48 h.The progress of the reaction was monitored by TLC. After the completion of the reaction, the reaction mixture was poured into a beaker containing ice cold water and stirred well, the separated solid filtered to dryness and purified through column chromatography of silica gel (60-120 mesh)using pet. ether and ethyl acetate (7:3) mixture as eluent,which afforded the products 3a-j in pure form.

References: [1]Medicinal Chemistry,2015,vol. 11,p. 789 - 797.

34
[ 70049-46-6 ]
2,4-dichloro-6-methoxy-5-nitroquinoline [ No CAS ]