6942-98-9|5-Chloro-8-nitroquinoline| Ambeed

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Quality Control of [ 6942-98-9 ] Purity: 95% SDS Specification

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Product Details of [ 6942-98-9 ]

CAS No. :	6942-98-9
Formula :	C₉H₅ClN₂O₂
M.W :	208.60
SMILES Code :	O=[N+](C1=C2N=CC=CC2=C(Cl)C=C1)[O-]
MDL No. :	MFCD00552691
InChI Key :	DHRPLGHWWKFRKY-UHFFFAOYSA-N
Pubchem ID :	242755

Safety of [ 6942-98-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305-P351-P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 6942-98-9 ]

* 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.

Downstream synthetic route of [ 6942-98-9 ]

[ 6942-98-9 ] Synthesis Path-Downstream 1~35

1
[ 6942-98-9 ]
[ 124-41-4 ]
[ 36020-53-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	In methanol; at 81℃; for 2.0h;	General Procedure 21: 5-Methoxy-8-nitroquinoline (Intermediate 66)Sodium methoxide (571 mg, 1.05 mmol) was added to a solution of <strong>[6942-98-9]5-chloro-8-nitroquinoline</strong> (Intermediate 65) (550 mg, 2.64 mmol) in MeOH (15 ml) and heated to 81 C. for 2 h. After cooling, the mixture was concentrated in vacuo, water was added and the mixture was extracted with DCM. The organic phase was dried (Na2SO4) and concentrated in vacuo gave the title compound (500 mg, 93%). The structure was confirmed by 1H NMR.
93%	In methanol; at 80℃; for 2.0h;	General Procedure 142: 5-methoxy-8-nitroquinoline (Intermediate 585)NaOMe (570 mg, 10.5 mmol) was added to a solution of <strong>[6942-98-9]5-chloro-8-nitroquinoline</strong> 27 (550 mg, 2.64 mmol) in MeOH (15 ml) and the mixture was heated at 80 C. for 2 h. The solvent was removed in vacuo and the residue was diluted with water and the aqueous phase was extracted with DCM. The organic phase was washed with brine and concentrated in vacuo to give the title compound (500 mg, 93%) which was used in the next step without further purification.MW: 204.19HPLCMS (Method C): [m/z]: 205
83%	In methanol; at 100℃; for 0.166667h;Micrwave irradiation;	2. Synthesis of 5-methoxy-8-nitro-quinoline (44); A mixture of sodium methoxide (7.3 g, 135.7 mmol) and <strong>[6942-98-9]5-chloro-8-nitroquinoline</strong> 43 (6.7 g , 32.2 mmol), in anhydrous MeOH (80 ml), was heated in a microwave oven (power: 250W, ramp time: 5 minutes) at 1000C for 10 minutes. The solvent was partially evaporated and CH2CI2 and water were added. The organic layer was collected and washed with water and brine, dried (Na2SO4) and evaporated. The residue was treated with MeOH/hexane (3:50) to afford 5- methoxy-8-nitroquinoline 44 (5.8 g, 83%) as a brown solid.1H-NMR (400 MHz, CDCI3, ppm): 9.08 (H-2, dd, 1 H, J=1.8 and 4.2 Hz), 8.63 (H-4, dd, 1 H, J=1.8 and 8.6 Hz), 8.19 (H-7, d, 1 H, J=8.6 Hz), 7.51 (H-3, dd, 1 H, J=4.2 and 8.6 Hz), 6.84 (H-6, d, 1 H, J=8.6 Hz), 4.09 (OCH3, s, 3H).

67%

In methanol; at 70℃; for 5.0h;Inert atmosphere;

Specifically, first, in a two-neck eggplant-shaped flask of <strong>[6942-98-9]5-chloro-8-nitroquinoline</strong> (0.87 g, 4.21 mmol), sodium methoxide (0.95g, 17.65mmol) were under nitrogen was added a dehydrated methanol It was added 30ml.After reacted for 5 hours at 70 C., the solvent was removed by an evaporator, and extracted into an organic layer was separated with dichloromethane and water.The organic layer was washed with brine, dehydrated by adding sodium sulfate to give Removal of the solvent a brown oil.The oil, an alumina column (developing solvent: hexane: ethyl acetate = 10: 1) was purified using a result obtained by removing the solvent by an evaporator, ocher solid was in a yield of 0.484 g, yield 67%,

References: [1]Patent: US2012/214803,2012,A1 .Location in patent: Page/Page column 130.
[2]Patent: US2012/214803,2012,A1 .Location in patent: Page/Page column 142.
[3]Patent: WO2010/66832,2010,A1 .Location in patent: Page/Page column 31.
[4]Patent: JP5659191,2015,B2 .Location in patent: Paragraph 0077; 0078; 0079; 0080.
[5]Journal of Organic Chemistry,1947,vol. 12,p. 799,804.
[6]Angewandte Chemie - International Edition,2013,vol. 52,p. 11124 - 11128.
Angew. Chem.,2013,vol. 125,p. 11330 - 11334,5.
[7]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453.

2
[ 6942-98-9 ]
[ 5432-09-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic acid; zinc; In dichloromethane; at 0℃; for 2.0h;	A mixture of <strong>[6942-98-9]5-chloro-8-nitroquinoline</strong> (5 g, 23.97 mmol), and Zn (14.4 g, 239.69 mmol) in DCM (200 mL) was cooled to 0C, followed by dropwise addition of AcOH (15.7 g, 239.69 mmol). The reaction mixture was stirred at 0C for 2 hr then filtered. The filtrate was concentration under reduced pressure. The residue was purified via flash column chromatography, yielding the desired product (3.5 g, 82% yield). LC-MS: m/z 179 (M+H)+.
67%	With tin(II) chloride dihdyrate; In ethanol; at 20℃; for 2.5h;Inert atmosphere;	first, in 100mL two-neck eggplant type flask <strong>[6942-98-9]5-chloro-8-nitroquinoline</strong> (2.016g, 9.83mmol) was placed and dissolved in ethanol 40 mL.The reaction vessel was replaced with nitrogen and stannous (11.1 g, 49.1 mmol) chloride was added, and stirred for 2.5 hours at room temperature.Under stirring, cold water, further saturated aqueous sodium carbonate was added, basified, and separatory extraction with dichloromethane.The organic layer was concentrated with an evaporator to obtain a vacuum-dried brown solid was in a yield of 1.1 g and a yield of 67%,
10.2 g	With iron; acetic acid; at 65℃; for 2.0h;Inert atmosphere;	5-Chloro-8-nitroquinoline (13.8 g, 66 mmol) was dissolved in 180 mL of acetic acid, and the ironpowder (25 g, 455 mmol) was added to the solution. The mixture was heated to 65 C for 2 h undernitrogen. The reaction was filtered through a celite pad, and washed with ethyl acetate. The filtratewas concentrated in vacuo. The resulting brown gum was dissolved in 200 mL of DCM, and basifiedby 4N NaOH aq. until pH. 10, and the solution was filtered through a celite pad, and filtrate wasextracted with DCM (3x). The combined organic layer was washed with brine and dried byanhydrous Na2SO4, and concentrated in vacuo to give 5-chloroquinolin-8-amine (10.2 g, 57 mmol,87%).

References: [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1679 - 1688.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 15509 - 15512.
[3]Patent: WO2016/40764,2016,A1 .Location in patent: Paragraph 0151.
[4]Journal of the American Chemical Society,2021,vol. 143,p. 14021 - 14021.
[5]Chemistry - A European Journal,2013,vol. 19,p. 14697 - 14701.
[6]Patent: JP5659191,2015,B2 .Location in patent: Paragraph 0070; 0071; 0072.
[7]Justus Liebigs Annalen der Chemie,1913,vol. 396,p. 63.
[8]Justus Liebigs Annalen der Chemie,1913,vol. 396,p. 63.
[9]Chemistry Letters,2015,vol. 44,p. 1365 - 1367.
[10]Chemical Communications,2016,vol. 52,p. 6423 - 6426.

3
[ 6942-98-9 ]
[ 5432-09-7 ]
[ 36107-01-4 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1592.

4
[ 6942-98-9 ]
[ 129717-35-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium hydroxide; at 100℃; for 2.0h;	General Procedure 134: 8-Nitro-quinolin-5-ol (Intermediate 563)KOH (2.69 g, 47.9 mmol) was added to a solution of 5-chloro-8-nitro-quinoline 27 (1.0 g, 4.79 mmol) in EtOH (20 ml) and water (30 ml) and the mixture was heated at 100 C. for 2 h. The reaction mixture was cooled in the fridge for 18 h and the resulting crystals were collected by filtration and dried to give the title compound (616 mg, 68%).MW: 190.16HPLCMS (Method B):[m/z]: 191.15

References: [1]Patent: US2012/214803,2012,A1 .Location in patent: Page/Page column 184.
[2]Journal of Organic Chemistry,1947,vol. 12,p. 799,804.
[3]Journal of Organic Chemistry,1947,vol. 12,p. 799,804.

5
[ 6942-98-9 ]
bis-(8-nitro-[5]quinolyl)-sulfide [ No CAS ]

References: [1]Journal of the American Chemical Society,1940,vol. 62,p. 173.

6
[ 67-56-1 ]
[ 6942-98-9 ]
[ 42606-39-3 ]
[ 36020-53-8 ]

References: [1]Liebigs Annalen der Chemie,1993,p. 823 - 830.

7
[ 6942-98-9 ]
[ 42606-39-3 ]
[ 36020-53-8 ]

References: [1]Liebigs Annalen der Chemie,1993,p. 823 - 830.

8
[ 110-91-8 ]
[ 6942-98-9 ]
4-(8-nitroquinolin-5-yl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In dimethyl sulfoxide; at 110℃; for 4.0h;	Synthetic Method 4 5-morpholin-4-yl-8-nitro-quinoline (precursor to Example Compounds 9, 52, 53); A stirred solution of 5-chloro-8-nitro-quinoline (6.00 g, 28.8 mmol) and morpholine (7.5 mL, 86 mmol) in dimethylsulfoxide (30 mL) was heated at 110 C. for 4 hours. The reaction solution was cooled and then partitioned between ethyl acetate and water. The organic layer was washed with water, dried (sodium sulfate) and concentrated to afford 7.20 g (96%) of crude product, which was used without further purification, as an orange-brown solid: 1H NMR (CDCl3) δ 9.07-9.04 (m, 1H), 8.53-8.48 (m, 1H), 8.09 (d, J=8.3 Hz, 1H), 7.52 (dd, J=8.7, 4.2 Hz, 1H), 7.07 (d, J=8.3 Hz, 1H), 4.03-3.95 (m, 4H), 3.22-3.13 (m, 4H) ppm.
	In dimethyl sulfoxide; at 100℃; for 18.0h;	General Procedure 141: 5-Morpholin-4-yl-8-nitro-quinoline (Intermediate 580)Morpholine (251.6 μl, 2.88 mmol) was added to a solution of 5-chloro-8-nitro-quinoline 27 (200 mg, 0.96 mmol) in DMSO (2 ml) and the mixture was heated at 100 C. in a sealed tube for 18 h. After cooling, the mixture was diluted with water (10 ml) and the resulting precipitate was collected by filtration. The solid was dried in vacuo to give the title compound (200 mg, 81%) which was used in the next step without further purification.MW: 259.26HPLCMS (Method B):[m/z]: 260.35

References: [1]Patent: US2007/254894,2007,A1 .Location in patent: Page/Page column 21.
[2]Patent: US2012/214803,2012,A1 .Location in patent: Page/Page column 185-186.

9
[ 6942-98-9 ]
[ 108-95-2 ]
[ 138042-88-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium hydride; In N,N-dimethyl-formamide; for 5.0h;	Synthetic Method 6 8-nitro-5-phenoxy-quinoline (precursor to Example Compound 12); To a stirred solution of phenol (0.244 g, 2.59 mmol) and 5-chloro-8-nitro-quinoline (0.450 g, 2.16 mmol) in N,N-dimethylformamide (5.0 mL) was added sodium hydride (0.120 g of 60% dispersion in mineral oil, 3.00 mmol). After 5 hours, the reaction was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was dried (sodium sulfate) and concentrated to afford a moist, yellow-brown solid. The crude product was triturated with hexanes/ethyl acetate to afford 0.438 g (76%) of product as a mustard colored solid: 1H NMR (CDCl3) δ 9.15 (dd, J=4.2, 1.6 Hz, 1H), 8.79 (dd, J=8.5, 1.6 Hz, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.63-7.57 (m, 1H), 7.52-7.44 (m, 2H), 7.35-7.27 (m, 1H), 7.17 (d, J=8.0 Hz, 2H), 6.75 (d, J=8.6 Hz, 1H) ppm.

References: [1]Patent: US2007/254894,2007,A1 .Location in patent: Page/Page column 21.

10
[ 6942-98-9 ]
5-(methylamino)-6,8-dinitroquinoline [ No CAS ]

References: [1]Liebigs Annalen der Chemie,1993,p. 823 - 830.

11
[ 6942-98-9 ]
acetic acid-(8-nitro-[5]quinolyl ester) [ No CAS ]

References: [1]Journal of Organic Chemistry,1947,vol. 12,p. 799,804.
[2]Journal of Organic Chemistry,1947,vol. 12,p. 799,804.

12
[ 6942-98-9 ]
N-(5-chloroquinolin-8-yl)acetamide [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1913,vol. 396,p. 63.
[2]Patent: WO2016/40764,2016,A1 .

13
[ 5443-33-4 ]
[ 6942-98-9 ]

References: [1]Bulletin de la Societe Chimique de France,1930,vol. <4> 47,p. 749.
[2]Journal of the American Chemical Society,1946,vol. 68,p. 1322.

14
[ 6942-98-9 ]
[ 30465-68-0 ]

References: [1]Organic Letters,2014,vol. 16,p. 4956 - 4959.
[2]Patent: JP5659191,2015,B2 .
[3]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453.

15
[ 6942-98-9 ]
[ 1394085-71-2 ]

References: [1]Patent: US2012/214803,2012,A1 .

16
[ 6942-98-9 ]
C₁₁H₈BrClN₂O [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14697 - 14701.
[2]Patent: JP5659191,2015,B2 .

17
[ 6942-98-9 ]
2-[bis(pyridin-2-ylmethyl)]amino-N-(5-chloroquinolin-8-yl)acetamide [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14697 - 14701.
[2]Patent: JP5659191,2015,B2 .

18
[ 6942-98-9 ]
C₂₄H₁₂⁽²⁾H₇ClN₂O [ No CAS ]