[ CAS No. 201420-30-6 ] {[proInfo.proName]}

Name: 201420-30-6|4-Chloroquinoline-3-carbaldehyde|95%
Brand: Ambeed
SKU: A395490
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Quality Control of [ 201420-30-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 201420-30-6 ]

SDS Specification

Alternatived Products of [ 201420-30-6 ]

Product Details of [ 201420-30-6 ]

CAS No. :	201420-30-6	MDL No. :	MFCD03787717
Formula :	C₁₀H₆ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PTCAOHUEDACTEB-UHFFFAOYSA-N
M.W :	191.61	Pubchem ID :	1478030
Synonyms :

Calculated chemistry of [ 201420-30-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.14
TPSA :	29.96 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	2.28
Log Po/w (WLOGP) :	2.7
Log Po/w (MLOGP) :	1.7
Log Po/w (SILICOS-IT) :	3.22
Consensus Log Po/w :	2.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.97
Solubility :	0.206 mg/ml ; 0.00108 mol/l
Class :	Soluble
Log S (Ali) :	-2.55
Solubility :	0.545 mg/ml ; 0.00284 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.27
Solubility :	0.0103 mg/ml ; 0.000054 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.25

Safety of [ 201420-30-6 ]

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 [ 201420-30-6 ]

* 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 [ 201420-30-6 ]

[ 201420-30-6 ] Synthesis Path-Downstream 1~77

1
[ 551-93-9 ]
[ 68-12-2 ]
[ 201420-30-6 ]

Yield	Reaction Conditions	Operation in experiment
60%		A formylation mixture was prepared from 41.2 mL (444.4 mmol, 6.00 mol eq) of POCl3 that was added dropwise to 90.0 mL of DMF (abs) at 0 C. Resulted solution was stirred for 15 min under Ar at rt. Then 9.0 mL (74.0 mmol,1.00 mol eq) of 1-(2-aminophenyl)ethanone was added dropwise to the stirred formylation mixture within 30 min and the mixture heated to 60 C for 16 h (instead of 4 h, described previously in the literature) (Seixas et al. 2011). Then, the mixture was cooled to rt by adding 400 g of crashed ice in 200 mL H2O and the reaction neutralized to pH 7 by solid NaHCO3. Precipitated yellow product was filtered off, dissolved in CHCl3, extracted with water. A separated organic layer was dried over Na2SO4, filtered, concentrated by RVO and HV. Crystallization from EA with charcoal bleaching provided 8.50 g (44.4 mmol, 60%) of 4-chloroquinoline-3-carbaldehyde in form of a white solid material. A suspension of the crude 4-chloroquinoline-3-carbaldehyde in 80 mL of HCOOH (54%aqueous) was hydrolyzed at 50 C within 2 h. The mixture was cooled down and left in refrigerator overnight. The formed solid product was filtered off, washed with H2O, Et2O and dried under HV. The 1,4-dihydro-4-oxoquinoline-3-carbaldehyde (1a) was obtained as a white solid 7.15 g (41.23 mmol, 93 or 56%overallyield) and used for further synthetic step (Scheme 1).
50%		General procedure: POCl3 (16.1 g, 0.105 mol) was added dropwise to DMF (10 mL) at 0 C, and the resulting mixture was stirred for 15 min under N2 at r.t. A solution of the appropriate 1-(2-aminophenyl)ethanone 1 (15.0mmol) in DMF (10 mL) was added dropwise from a syringe, and the mixture was heated at 90 C for 12 h. After it had been cooled to r.t., the mixture was distilled to remove excess POCl3. The viscous oily residue was slowly added to crushed ice, and the mixture was neutralized with sat. aq NaHCO3. The product was extracted with CHCl3 (2 × 50 mL) and the combined organic phases were washed with water, dried (MgSO4), filtered, and concentrated. The residue was driedin vacuo to give a crude product that was purified by column chromatography(silica gel).
43%	With trichlorophosphate; at 0 - 90℃; for 4h;	To a 00C solution of l-(2-aminophenyl)ethan-l-one (2.0 g, 14.8 mmol) in anhydrous DMF (10 mL) was added dropwise phosphorus oxychloride (5.5 mL, 59.2 mmol). The reaction mixture was stirred at room temperature for 1 hour and at 900C for 3 hours. After cooling to room temperature, the mixture was poured in a mixture of ice/water/NH4OAc to neutralize. The mixture was stirred at room temperature overnight. The product was recovered by filtration and washed with water (2 x 20 mL). The solid material was dissolved in ethyl acetate (100 mL). The solution was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 4- chloroquinoline-3-carbaldehyde (1.2 g, 43% yield). The product was used without further purification.

		General procedure: (E)-3-styrylquinolin-4(1H)-ones 1a-1k and 1t were prepared according to theliterature procedure (Scheme 1).1, 2 POCl3 (123.4 mmol) was added dropwise to 25mL dry N,N-dimethylformamide (DMF) at 0 C under argon, and the mixture wasstirred for 15 min at room temperature. Then a solution of 3 1-(2-aminophenyl)ethanones (20.6 mmol) in dry DMF (3 mL) was added dropwise. The reactionsolution was heated to 60 C and stirred for 4 h. The reaction was stopped by pouredinto 100 g ice and 100 mL water, and neutralized with NaHCO3. The formed solid wasfiltered off, dissolved into 200 mL CH2Cl2 and washed with 3 × 200 mL water. Theorganic layer was dried over Na2SO4 and concentrated under reduced pressure. Theresulting solid was purified by column chromatography on silica gel (petroleum ether:ethyl acetate = 20:1-10:1) to afford 4-chloroquinoline-3-carbaldehydes 4.
	With trichlorophosphate; at 0 - 60℃; for 4h;	To an anh. DMF (20 ml_), POCI3 (8.27 ml_, 88.8 mmol, 6 eq) was added dropwise at 0C. Then 1-(2-aminophenyl)ethan-1-one (2.00 g, 14.8 mmol, 1 eq) in anh. DMF (5 ml.) was added drop- wise, and the reaction was heated for 4 h at 60C. Afterwards, the reactions was cooled down to 0C, quenched with water. Then solution was neutralized with saturated NaHCC>3 aqueous solution, diluted in water and extracted with DCM. The layers were separated. Organic layer was dried over MgS04, filtered off and concentrated in vacuo to afford the title compound (1.43 g, 7.49 mmol, yield 51 %) as an orange solid that was taken to the next step without additional purification. ESI-MS: 192 [M+H]+

Reference： [1]Chemical Papers,2018,vol. 72,p. 683 - 690
[2]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742
[3]Synthesis,2015,vol. 47,p. 3139 - 3146
[4]RSC Advances,2019,vol. 9,p. 20573 - 20581
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1997,vol. 36,p. 541 - 544
[6]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 94
[7]Organic Process Research and Development,2012,vol. 16,p. 1442 - 1448
[8]Synlett,2006,p. 3324 - 3328
[9]Synlett,2018,vol. 29,p. 1578 - 1582
[10]Patent: WO2019/238786,2019,A1 .Location in patent: Page/Page column 63-64

2
[ 68-12-2 ]
[ 5234-26-4 ]
[ 611-35-8 ]
[ 201420-30-6 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1997,vol. 36,p. 541 - 544

3
[ 201420-30-6 ]
[ 7509-12-8 ]

Yield	Reaction Conditions	Operation in experiment
7.15 g	With formic acid; In water; at 50℃; for 2h;	A formylation mixture was prepared from 41.2 mL (444.4 mmol, 6.00 mol eq) of POCl3 that was added dropwise to 90.0 mL of DMF (abs) at 0 C. Resulted solution was stirred for 15 min under Ar at rt. Then 9.0 mL (74.0 mmol,1.00 mol eq) of 1-(2-aminophenyl)ethanone was added dropwise to the stirred formylation mixture within 30 min and the mixture heated to 60 C for 16 h (instead of 4 h, described previously in the literature) (Seixas et al. 2011). Then, the mixture was cooled to rt by adding 400 g of crashed ice in 200 mL H2O and the reaction neutralized to pH 7 by solid NaHCO3. Precipitated yellow product was filtered off, dissolved in CHCl3, extracted with water. A separated organic layer was dried over Na2SO4, filtered, concentrated by RVO and HV. Crystallization from EA with charcoal bleaching provided 8.50 g (44.4 mmol, 60%) of <strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong> in form of a white solid material. A suspension of the crude <strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong> in 80 mL of HCOOH (54%aqueous) was hydrolyzed at 50 C within 2 h. The mixture was cooled down and left in refrigerator overnight. The formed solid product was filtered off, washed with H2O, Et2O and dried under HV. The 1,4-dihydro-4-oxoquinoline-3-carbaldehyde (1a) was obtained as a white solid 7.15 g (41.23 mmol, 93 or 56%overallyield) and used for further synthetic step (Scheme 1).
0.75 g	With formic acid; In water; at 50℃; for 2h;	<strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong> (1.10 g, 5.74 mmol, 1 eq) was suspended in 54% aqueous so- lution HCOOH (13.41 ml_). The reaction was carried out at 50C for 2 h. The resulting mixture was being frozen in a fridge for 16 h. Precipitate was filtered off and washed with water to give product (0.75 g, 4.33 mmol, yield 75%) as an orange solid. ESI-MS: 174 [M+H]+ 1H NMR (400 MHz, DMSO-ofe) d 12.69 (s, 1H), 10.20 (s, 1H), 8.49 (s, 1H), 8.22 (dd, J= 8.0, 1.5 Hz, 1H), 7.77 (m, 1H), 7.67 (dd, J= 8.3, 1.1Hz, 1H), 7.48 (m, 1H).

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742
[2]RSC Advances,2019,vol. 9,p. 20573 - 20581
[3]Synlett,2006,p. 3324 - 3328
[4]Synlett,2008,p. 3193 - 3197
[5]Chemical Papers,2018,vol. 72,p. 683 - 690
[6]Patent: WO2019/238786,2019,A1 .Location in patent: Page/Page column 64; 63

4
[ 65867-28-9 ]
[ 201420-30-6 ]
[ 1141888-59-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2008,vol. 44,p. 442 - 450

5
[ 68572-18-9 ]
[ 201420-30-6 ]
[ 1141888-59-6 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2008,vol. 44,p. 442 - 450

6
[ 38897-99-3 ]
[ 201420-30-6 ]
[ 1257983-10-0 ]
[ 1257983-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 1h;Reflux;	General procedure: A mixture of sodium hydride (6.0 mmol) and appropriate phosphonium halide(6.0 mmol) in 50 mL dry THF was refluxed 3 h (R2 = H, Me, F, Cl) or 1 h (R2 = OEt)under argon. When the solution turned into orange, and the suspension of thephosphonium salt disappeared, it indicated that ylide was formed. Subsequently,<strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong>s 4 (2.0 mmol) was added at the same temperatureunder magnetic stirring for 1 h. After the reaction mixture was cooled to roomtemperature, it was poured into 80 g ice and 80 mL water and acidified with 2M HClsolution until the pH was adjusted to 5. The mixture was extracted with 3 × 80 mLCH2Cl2 and then the organic phases were combined, dried over Na2SO4 andconcentrated under reduced pressure. The resulting solid was purified by columnchromatography on silica gel (petroleum ether: ethyl acetate = 30:1-15:1) to get 6-(Z)and 6-(E).

Reference： [1]Synlett,2010,p. 2257 - 2262
[2]Synlett,2018,vol. 29,p. 1578 - 1582

7
[ 38897-99-3 ]
[ 201420-30-6 ]
[ 1257983-17-7 ]

Reference： [1]Synlett,2010,p. 2257 - 2262

8
[ 6933-17-1 ]
[ 201420-30-6 ]
[ 1257983-12-2 ]
[ 1257983-16-6 ]

Reference： [1]Synlett,2010,p. 2257 - 2262

9
[ 6933-17-1 ]
[ 201420-30-6 ]
[ 1257983-19-9 ]

Reference： [1]Synlett,2010,p. 2257 - 2262

10
[ 16721-45-2 ]
[ 201420-30-6 ]
[ 1227000-48-7 ]

Reference： [1]Synlett,2010,p. 2257 - 2262

11
[ 16721-45-2 ]
[ 201420-30-6 ]
[ 1257983-09-7 ]
[ 1257983-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 1h;Reflux;	General procedure: A mixture of sodium hydride (6.0 mmol) and appropriate phosphonium halide(6.0 mmol) in 50 mL dry THF was refluxed 3 h (R2 = H, Me, F, Cl) or 1 h (R2 = OEt)under argon. When the solution turned into orange, and the suspension of thephosphonium salt disappeared, it indicated that ylide was formed. Subsequently,<strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong>s 4 (2.0 mmol) was added at the same temperatureunder magnetic stirring for 1 h. After the reaction mixture was cooled to roomtemperature, it was poured into 80 g ice and 80 mL water and acidified with 2M HClsolution until the pH was adjusted to 5. The mixture was extracted with 3 × 80 mLCH2Cl2 and then the organic phases were combined, dried over Na2SO4 andconcentrated under reduced pressure. The resulting solid was purified by columnchromatography on silica gel (petroleum ether: ethyl acetate = 30:1-15:1) to get 6-(Z)and 6-(E).

Reference： [1]Synlett,2010,p. 2257 - 2262
[2]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742
[3]Synlett,2018,vol. 29,p. 1578 - 1582

12
[ 150880-89-0 ]
[ 201420-30-6 ]
[ 1257983-11-1 ]
[ 1257983-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 1h;Reflux;	General procedure: A mixture of sodium hydride (6.0 mmol) and appropriate phosphonium halide(6.0 mmol) in 50 mL dry THF was refluxed 3 h (R2 = H, Me, F, Cl) or 1 h (R2 = OEt)under argon. When the solution turned into orange, and the suspension of thephosphonium salt disappeared, it indicated that ylide was formed. Subsequently,<strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong>s 4 (2.0 mmol) was added at the same temperatureunder magnetic stirring for 1 h. After the reaction mixture was cooled to roomtemperature, it was poured into 80 g ice and 80 mL water and acidified with 2M HClsolution until the pH was adjusted to 5. The mixture was extracted with 3 × 80 mLCH2Cl2 and then the organic phases were combined, dried over Na2SO4 andconcentrated under reduced pressure. The resulting solid was purified by columnchromatography on silica gel (petroleum ether: ethyl acetate = 30:1-15:1) to get 6-(Z)and 6-(E).

Reference： [1]Synlett,2010,p. 2257 - 2262
[2]Synlett,2018,vol. 29,p. 1578 - 1582

13
[ 150880-89-0 ]
[ 201420-30-6 ]
[ 1257983-18-8 ]

Reference： [1]Synlett,2010,p. 2257 - 2262

14
[ 676-58-4 ]
[ 201420-30-6 ]
[ 1258406-21-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5166 - 5173

15
[ 551-93-9 ]
[ 201420-30-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 5166 - 5173

16
[ 201420-30-6 ]
[ 21168-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 3h;	To a O0C solution of <strong>[201420-30-6]4-chloroquinoline-3-carbaldehyde</strong> (1.2 g, 6.3 mmol) in anhydrous methanol (20 mL) was added sodium borohydride (250 mg, 6.6 mmol). The reaction mixture was stirred at room temperature for 3 hours. Saturated ammonium chloride solution (20 mL) was added. The resultant mixture was extracted with dichloromethane (2 x 20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording (4- chloroquinolin-3-yl)methanol (1.0 g, 85% yield). The product was used without further purification.

Reference： [1]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 94-95

17
[ 201420-30-6 ]
[ 1133429-19-2 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742

18
[ 201420-30-6 ]
[ 1227000-53-4 ]
[ 1257982-98-1 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742

19
[ 201420-30-6 ]
[ 1257983-02-0 ]
[ 1257983-07-5 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742

20
[ 201420-30-6 ]
[ 1257982-97-0 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742
[2]RSC Advances,2019,vol. 9,p. 20573 - 20581

21
[ 201420-30-6 ]
[ 70027-78-0 ]

Reference： [1]Monatshefte fur Chemie,2011,vol. 142,p. 731 - 742
[2]Patent: WO2019/238786,2019,A1

22
[ 201420-30-6 ]
[ 1415989-59-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 6330 - 6333

23
[ 201420-30-6 ]
[ 1415989-28-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 6330 - 6333

24
[ 201420-30-6 ]
[ 1415989-41-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 6330 - 6333

25
[ 292638-85-8 ]
[ 201420-30-6 ]
[ 1415989-21-7 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 6330 - 6333

26
[ 201420-30-6 ]
3,4-dihydro-4-(1H-indol-3-yl)-2,3-diphenylbenzo[c][2,7]naphthyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3635 - 3638

27
[ 201420-30-6 ]
3,4-dihydro-4-(1H-indol-3-yl)-2-phenyl-3-p-tolylbenzo[c][2,7]naphthyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3635 - 3638

28
[ 201420-30-6 ]
3-(4-chlorophenyl)-3,4-dihydro-4-(1H-indol-3-yl)-2-phenylbenzo[c][2,7]naphthyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3635 - 3638

29
[ 201420-30-6 ]
3,4-dihydro-4-(5-methoxy-1H-indol-3-yl)-2,3-diphenylbenzo[c][2,7]naphthyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3635 - 3638

30
[ 201420-30-6 ]
4-(1-butyl-1H-indol-3-yl)-3,4-dihydro-2,3-diphenylbenzo[c][2,7]naphthyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3635 - 3638

31
[ 536-74-3 ]
[ 201420-30-6 ]
[ 1443234-34-1 ]

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 3635 - 3638

32
[ 201420-30-6 ]
[ 681215-57-6 ]
1-phenyl-1H-pyrazolo[4,3-c]quinoline [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

33
[ 201420-30-6 ]
1-(p-toluyl)-1H-pyrazolo[4,3-c]quinoline [ No CAS ]
4-(p-tolylamino)quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

34
[ 201420-30-6 ]
1-(4-methoxyphenyl)-1H-pyrazolo[4,3-c]quinoline [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146
[2]Synthesis,2015,vol. 47,p. 3139 - 3146

35
[ 201420-30-6 ]
1-(4-fluorophenyl)-1H-pyrazolo[4,3-c]quinoline [ No CAS ]
4-((4-fluorophenyl)amino)quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

36
[ 201420-30-6 ]
4-((4-fluorophenyl)amino)quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

37
[ 201420-30-6 ]
4-((3-fluorophenyl)amino)quinoline-3-carbonitrile [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

38
[ 201420-30-6 ]
1-methyl-1H-pyrazolo[4,3-c]quinoline [ No CAS ]

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

39
[ 59-88-1 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde phenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

40
[ 637-60-5 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde p-tolylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

41
[ 19501-58-7 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 4-methoxyphenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

42
[ 823-85-8 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 4-fluorophenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

43
[ 2924-16-5 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 3-fluorophenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

44
[ 1073-70-7 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 4-chlorophenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

45
[ 5446-18-4 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 2,4-dichlorophenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

46
[ 100-16-3 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 4-nitrophenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

47
[ 302-15-8 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde methylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine; In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

48
[ 5329-12-4 ]
[ 201420-30-6 ]
4-chloroquinoline-3-carboxaldehyde 2,4,6-trichlorophenylhydrazone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In ethanol; at 25℃;Inert atmosphere;	General procedure: A mixture of appropriate aldehyde 2 (0.30 mmol), hydrazine salt (0.30 mmol), and Et3N (30 mg, 0.30 mmol) in EtOH (20 mL) was stirred at 25 C overnight under N2. (In the case of hydrazine, the free base was used and the reaction was performed without addition ofEt3N.) The solvent was removed and the residue was crystallized from EtOH. The filter cake was collected and dried. An additional portion of the product obtained from the filtrate by evaporation of the solvent was purified by chromatography (silica gel). The two portions of pure product 3 were combined for subsequent use.

Reference： [1]Synthesis,2015,vol. 47,p. 3139 - 3146

49
[ 201420-30-6 ]
3-phenyl-2H-pyrano[3,2-c]quinolin-2-one [ No CAS ]