13067-94-2|2-Chloro-5-nitroquinoline| Ambeed

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Quality Control of [ 13067-94-2 ] Purity: 98% SDS Specification

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Product Details of [ 13067-94-2 ]

CAS No. :	13067-94-2
Formula :	C₉H₅ClN₂O₂
M.W :	208.60
SMILES Code :	[O-][N+](=O)C1=CC=CC2=C1C=CC(Cl)=N2
MDL No. :	MFCD18448913
InChI Key :	IICVTJMDHNPPOP-UHFFFAOYSA-N
Pubchem ID :	319251

Safety of [ 13067-94-2 ]

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

Application In Synthesis of [ 13067-94-2 ]

* 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 [ 13067-94-2 ]

[ 13067-94-2 ] Synthesis Path-Downstream 1~35

1
[ 110-89-4 ]
[ 13067-94-2 ]
5-nitro-2-piperidino-quinoline [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1943,vol. 63,p. 258,263.
Chemisches Zentralblatt,1951,vol. 122,p. 5153.

2
[ 13067-94-2 ]
[ 121-78-8 ]
2-diethylaminomethyl-4-(5-nitro-[2]quinolylamino)-phenol; dihydrochloride [ No CAS ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 1363,1372.
Journal of the American Chemical Society,1950,vol. 72,p. 1024.

3
[ 13067-94-2 ]
[ 2372-45-4 ]
[ 108239-41-4 ]

References: [1]Yaoxue Xuebao/Acta pharmaceutica Sinica,1959,vol. 7,p. 311,316.
Chem.Abstr.,1960,p. 17397.

4
[ 13067-94-2 ]
[ 108-24-7 ]
[ 650605-74-6 ]

References: [1]Journal of the American Pharmaceutical Association (1912),1946,vol. 35,p. 331,332.

5
[ 13067-94-2 ]
[ 106-47-8 ]
[ 874498-18-7 ]

References: [1]Journal of the Chemical Society,1949,p. 227,229.

6
[ 13067-94-2 ]
[ 607377-99-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tin(ll) chloride; In ethanol; at 80℃; for 4.0h;Inert atmosphere;	General procedure: Appropriate benzyl substituted compounds [37], 14a-b or 17g (1.0 equiv) was dissolved in ethanol and SnCl2 (3.0 equiv) was added. After the reaction mixture was stirred for 4hat 80C in argon gas environment, it was concentrated and partitioned between saturate brine and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and evaporated under the vacuum. The resulting residue was purified by silica gel column chromatography to afford 10a-l, 15a-b and 17h.
	With hydrogen;platinum(IV) oxide; In ethanol; at 20℃;	EXAMPLE 614-Fluoro-N-[2-(2-methoxy-benzylamino)-quinolin-5-yl]-benzenesulfonamideStep A5-Nitro-2-chloroquinoline (CAS 13067-94-2, 5.0 g, 24 mmol) was dissolved in 500 mL ethanol and platinumoxid hydrate (176 mg, 0.718 mmol) was added. He reaction mixture was hydrogenated with a hydrogen ballon at room temperature overnight and filtered. The filtrate was evaporated off. The crude 5-amino-2-chloroquinoline (4.58 g) was used without further purification for the next step.
	With hydrogen;platinum(IV) oxide; In ethanol; at 20℃;	5-Nitro-2-chloroquinoline (CAS 13067-94-2, 5.0 g, 24 mmol) was dissolved in 500 mL ethanol and platinumoxid hydrate (176 mg, 0.718 mmol) was added. The reaction mixture was hydrogenated with a hydrogen ballon at room temperature overnight and filtered. The filtrate was evaporated off. The crude 5-amino-2-chloroquinoline (4.58 g) was used without further purification for the next step.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 151,p. 462 - 481.
[2]Journal of the American Chemical Society,1938,vol. 60,p. 2104.
[3]Patent: US2008/81907,2008,A1 .Location in patent: Page/Page column 27.
[4]Patent: US2008/146567,2008,A1 .Location in patent: Page/Page column 12; 18-19.

7
[ 13067-94-2 ]
[ 6938-27-8 ]

References: [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 75 - 86.
[2]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 379.

8
[ 13067-94-2 ]
5-nitro-[2]quinolylamine [ No CAS ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1916,vol. <2> 93,p. 379.

9
[ 13067-94-2 ]
bis-(5-nitro-[2]quinolyl)-sulfide [ No CAS ]
[ 113942-93-1 ]

References: [1]Journal of the American Pharmaceutical Association (1912),1946,vol. 35,p. 331,332.

10
[ 7613-19-6 ]
[ 13067-94-2 ]

Yield	Reaction Conditions	Operation in experiment
42%	With trichlorophosphate; for 3.0h;Cooling with ice; Reflux;	Synthesis of 79 To 78 (4.94 g, 26 mmol), phosphorus oxyschloride (22 ml) was added dropwise under ice cooling and stirring, and the mixture was heated at reflux for 3 hours. The reaction solution was ice-cooled and ice water was added, and then the solution was made basic with ammonia water and extracted with chloroform. The extraction liquid was washed with saturated saline and dried, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel flash column chromatography (eluting solvent: n-hexane/methylene chloride = 2/1, 1/1, 1/2) and then washed with n-hexane to obtain 79 (2.25 g, 42%) as a pale yellow solid. APCI-MS m/z 209/211[M+H]+

References: [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1606 - 1611.
[2]Patent: EP2634177,2013,A1 .Location in patent: Paragraph 0254; 0256.
[3]Journal of the American Pharmaceutical Association (1912),1946,vol. 35,p. 331,332.
[4]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1943,vol. 63,p. 280.
Chem.Abstr.,1951,p. 5152.

11
[ 607-34-1 ]
[ 13067-94-2 ]

References: [1]Journal of the American Pharmaceutical Association (1912),1946,vol. 35,p. 331,332.
[2]Patent: EP2634177,2013,A1 .
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 1606 - 1611.

12
[ 13067-94-2 ]
[ 107415-52-1 ]

References: [1]Yaoxue Xuebao/Acta pharmaceutica Sinica,1959,vol. 7,p. 311,316.
Chem.Abstr.,1960,p. 17397.

13
[ 13067-94-2 ]
N-(4-chloro-phenyl)-N-(5-nitro-[2]quinolyl)-acetamide [ No CAS ]

References: [1]Journal of the Chemical Society,1949,p. 227,229.

14
[ 13067-94-2 ]
N-(4-chloro-phenyl)-N-(5-nitro-[2]quinolyl)-benzamide [ No CAS ]

References: [1]Journal of the Chemical Society,1949,p. 227,229.

15
[ 176976-31-1 ]
[ 13067-94-2 ]
(+)-(4AR)-(10BR)-4-methyl-8-(5-nitro-2-quinolinylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29 mg (56%)	With potassium carbonate; In N-methyl-acetamide;	EXAMPLE 169 (+)-(4aR)-(10bR)-4-methyl-8-(5-nitro-2-quinolinylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one STR186 A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-mercapto-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (31 mg, 0.12 mmol), potassium carbonate (158 mg, 1.14 mmol), <strong>[13067-94-2]2-chloro-5-nitroquinoline</strong> (30 mg, 0.14mmol) and 1 mL of anhydrous dimethylformamide, fitted with a reflux condenser, and the stirred mixture was heated at 60, under nitrogen, for 18 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 29 mg (56%) of the title compound as an amorphous foam. mp 149-154. FDMS: m/e=433. alpha[D]589 =+60.00 (c=0.10, chloroform).
29 mg (56%)	With potassium carbonate; In N-methyl-acetamide;	EXAMPLE 169 (+)-(4aR)-(10bR)-4-methyl-8-(5-nitro-2-quinolinylthio)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-mercapto-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (31 mg, 0.12 mmol), potassium carbonate (158 mg, 1.14 mmol), <strong>[13067-94-2]2-chloro-5-nitroquinoline</strong> (30 mg, 0.14 mmol) and 1 mL of anhydrous dimethylformamide, fitted with a reflux condenser, and the stirred mixture was heated at 60, under nitrogen, for 18 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 29 mg (56%) of the title compound as an amorphous foam. mp 149-154. FDMS: m/e=433. alpha[D]589 =+60.00 (c=0.10, chloroform).

References: [1]Patent: US5578724,1996,A .
[2]Patent: US5629007,1997,A .

16
[ 13067-94-2 ]
[ 10277-74-4 ]
[ 1032280-24-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	at 120℃;	Step A 5-Nitro-2-chloroquinoline (CAS 13067-94-2, 2.4 g, 11.5 mmol) and (R)-1-aminoindane (3.13 g, 23.5 mmol) were stirred in a sealed tube at 120 C. overnight. The reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->50:50 gradient). (R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine was obtained as a brown solid (2.67 g, 76%), MS: m/e=306.2 (M+H+).
76%	at 120℃;	Step A: 5-Nitro-2-chloroquinoline (CAS 13067-94-2, 2.4 g, 11.5 mmol) and (R)-1-aminoindane (3.13 g, 23 mmol) were stirred in a sealed tube at 120 C. overnight. The reaction mixture was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0?50:50 gradient). (R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine was obtained as a brown solid (2.67 g, 76%), MS: m/e=306.3 (M+H+).

References: [1]Patent: US2008/146567,2008,A1 .Location in patent: Page/Page column 22.
[2]Patent: US2009/227584,2009,A1 .Location in patent: Page/Page column 12.

17
[ 13067-94-2 ]
[ 6938-27-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With perchloric acid; In water; acetonitrile; at 100℃; for 72.0h;	General procedure: Acetonitrile (25?mL) and 70% perchloric acid solution (25?mL) were added onto 1 equiv. of the quinoline derivatives. The reaction mixture was stirred at 100?C overnight. The reaction mixture was then poured into ice, neutralized with KOH and extracted twice with dichloromethane. The organic layer was washed with water, dried over anhydrous MgSO4 and evaporated in vacuo. The crude residues were purified by chromatography on silica gel using adapted eluent and recrystallized if necessary to give compounds 7, 14, 19, 20. 4-methyl-8-nitroquinolin-2(1H)-one 7 (C10H8N2O3) was isolated and recrystallized in acetonitrile to yield a yellow solid (92%, 11?mmol, 2.2?g).
82%	With hydrogenchloride; In water; for 16.0h;Heating / reflux;Product distribution / selectivity;	A solution of <strong>[13067-94-2]2-chloro-5-nitroquinoline</strong> (1.92 mmol) in 10% hydrochloric acid (50 mL)was heated at reflux for 16 h. The insoluble solids were removed by filtration and the filtrate was extracted with ethyl acetate (5 x 100 mL). The combined organic layers were washed with brine (50 mL) and concentrated to provide 5-nitro-2-oxo-1,2-dihydroquinoline in 82% yield as a yellow solid.
82%	With hydrogenchloride; water; for 16.0h;Reflux;	2. Synthesis of 5-nitro-2-oxo-l,2-dihvdroquinoline.A solution of <strong>[13067-94-2]2-chloro-5-nitroquinoline</strong> (1.92 mmol) in 10% hydrochloric acid (50 mL)was heated at reflux for 16 h. The insoluble solids were removed by filtration and the filtrate was extracted with ethyl acetate (5 x 100 mL). The combined organic layers were washed with brine (50 mL) and concentrated to provide 5-nitro-2-oxo-l,2-dihydroquinoline in 82% yield as a yellow solid.

82%

With hydrogenchloride; water; for 16.0h;Reflux;

2. Synthesis of 5-nitro-2-oxo-l,2-dihydroquinoline.A solution of [13067-94-2]2-chloro-5-nitroquinoline (1.92 mmol) in 10% hydrochloric acid (50 mL)was heated at reflux for 16 h. The insoluble solids were removed by filtration and the filtrate was extracted with ethyl acetate (5 x 100 mL). The combined organic layers were washed with brine (50 mL) and concentrated to provide 5-nitro-2-oxo-l,2-dihydroquinoline in 82% yield as a yellow solid.

References: [1]European Journal of Medicinal Chemistry,2018,vol. 155,p. 135 - 152.
[2]Patent: WO2009/23844,2009,A2 .Location in patent: Page/Page column 108.
[3]Patent: WO2010/21797,2010,A1 .Location in patent: Page/Page column 71.
[4]Patent: WO2010/24980,2010,A1 .Location in patent: Page/Page column 89; 90.

18
[ 612-62-4 ]
[ 13067-94-2 ]

Yield	Reaction Conditions	Operation in experiment
19%	With sulfuric acid; nitric acid; at 0 - 40℃; for 0.833333h;	A solution of nitric acid (16 mL) and sulfuric acid (8 mL) was added over period of 20 min to a solution of 2-chloroquinoline (61.1 mmol) in sulfuric acid (150 mL) at 0 C. The reaction mixture was heated at 40 C for 30 min and was quenched with ice water (800 mL). The precipitated solids were collected by filtration and purified by Flash chromatography (20/1 petroleum ether/ethyl acetate) to provide 2-chloro-5-nitroquinoline in 19% yield as a yellow solid.
19%	With sulfuric acid; nitric acid; at 0 - 40℃;	20: Synthesis of 2-oxo-l,2-dihydroquinoline-5-sulfonyl chloride.1. Synthesis of 2-chloro-5-nitroquinoline.A solution of nitric acid (16 mL) and sulfuric acid (8 mL) was added over period of 20 min to a solution of 2-chloroquinoline (61.1 mmol) in sulfuric acid (150 mL) at 0 0C. The reaction mixture was heated at 40 0C for 30 min and was quenched with ice water (800 mL). The precipitated solids were collected by filtration and purified by Flash chromatography (20/1 petroleum ether/ethyl acetate) to provide 2-chloro-5-nitroquinoline in 19% yield as a yellow solid.
19%	With sulfuric acid; nitric acid; at 0 - 40℃;	1. Synthesis of 2-chloro-5-nitroquinoline.A solution of nitric acid (16 mL) and sulfuric acid (8 mL) was added over period of 20 min to a solution of 2-chloroquinoline (61.1 mmol) in sulfuric acid (150 mL) at 0 0C. The reaction mixture was heated at 40 0C for 30 min and was quenched with ice water (800 mL). The precipitated solids were collected by filtration and purified by Flash chromatography (20/1 petroleum ether/ethyl acetate) to provide 2-chloro-5-nitroquinoline in 19% yield as a yellow solid.

With sulfuric acid; nitric acid; at -10 - 20℃; for 1.33h;

To a solution of 12b (5.00 g, 30.6 mmol) in H2SO4 (15 mL) was added HNO3 (2.04 mL, 45.9 mmol) at -10 C and the reaction mixture was stirred at -10 C for 20 min and at room temperature for 1 h. The mixture was poured into crushed-ice, filtered and, washed with water. The obtained crude title compound (5.64 g), which was used in the following reaction without further purification.

References: [1]Patent: WO2009/23844,2009,A2 .Location in patent: Page/Page column 108.
[2]Patent: WO2010/21797,2010,A1 .Location in patent: Page/Page column 71.
[3]Patent: WO2010/24980,2010,A1 .Location in patent: Page/Page column 89.
[4]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 6559 - 6578,20.

19
[ 6850-57-3 ]
[ 13067-94-2 ]
[ 1186367-16-7 ]

Yield	Reaction Conditions	Operation in experiment
50%	at 120℃;	5-Nitro-2-chloroquinoline (CAS 13067-94-2,3 g, 14 mmol) and 2-methoxy-benzylamine (4.2 g, 31 mmol) were stirred in a sealed tube at 120 C. overnight. The reaction mixture was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0?30:70 gradient). (2-Methoxy-benzyl)-(5-nitro-quinolin-2-yl)-amine was obtained as a yellow solid (2.2 g, 50%), MS: m/e=310.1 (M+H+).

References: [1]Patent: US2009/227628,2009,A1 .Location in patent: Page/Page column 10.

20
[ 695-34-1 ]
[ 13067-94-2 ]
[ 1258453-51-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In tert-butyl alcohol;	Example 2: compound (64) of table IAccording to route (A), a mixture of <strong>[13067-94-2]2-chloro-5-nitroquinoline</strong> (100.0 mg) and 2-amino-4-methylpyridine (57.6mg), Pd2dba3 (20mg), XantPhos (30mg) and K2CO3 (270mg) in 3mL of t-BuOH gave compound (64) (14.0mg).

References: [1]Patent: WO2010/143168,2010,A2 .Location in patent: Page/Page column 65.

21
[ 13067-94-2 ]
[ 7439-89-6 ]
[ 607377-99-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In acetic acid;	5(iv) 2-Chloro-5-aminoquinoline (11) 2-Chloro-5-nitroquinoline (300 mg, 1.44 mmol) was added to glacial acetic acid (3 mL) and stirred at 65 C. Iron powder (403 mg) was added to the mixture and stirring continued for 5 h. The reaction mixture was then cooled, concentrated and the residue diluted with water (20 mL) and pH was adjusted by addition of sodium carbonate solution. The product was then extracted with ethyl acetate (3*15 mL). The combined extractes were washed with brine, dried over anhydrous sodium sulphate, filtered and evaporated to give the product as a brown oil (260 mg>90% yield). 1H-NMR (300 MHz, CDCl3) delta=8.11 (1H, d, J=9 Hz, Ar-H), 7.55-7.44 (2H, m, Ar-H), 7.30 (1H, d, J=9 Hz, Ar-H), 6.82 (1H, d, J=9 Hz, Ar-H). LCMS Mass Found=[M+H)+ 179, Calcd for C9H7N2Cl 178.

References: [1]Patent: US2011/27178,2011,A1 .

22
[ 697738-97-9 ]
[ 59-31-4 ]
[ 13067-94-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	With trichlorophosphate; In 1,2-dichloro-benzene;	5(iii) 2-Chloro-5-nitroquinoline (10) Phosphorous oxychloride (25 mL) was added slowly to a solution of carbostyril 9 (1.5 g, 7.35 mmol) in o-dichlorobenzene at 0 C. and then refluxed for 12 h. The reaction mixture was then quenched by pouring into the ice-cold water and then extracted with chloroform. Solvent was then dried over anhydrous sodium sulphate, filtered and evaporated to obtain a gummy residue. The product was obtained as a light brown solid by trituration with water (520 mg, 34% yield). 1H-NMR (300 MHz, CDCl3) delta=9.02 (1H, d, J=9 Hz, Ar-H), 8.43 (1H, d, J=9 Hz, Ar-H), 8.36 (1H, d, J=9 Hz, Ar-H), 7.87 (1H, t, J=9 Hz, Ar-H, 7.66 (1H, d, J=9 Hz, Ar-H). LCMS Mass Found=[M+H)+ 209, Calcd for C9H5N2O2Cl 208.

References: [1]Patent: US2011/27178,2011,A1 .

23
[ 685886-67-3 ]
[ 13067-94-2 ]
[ 1395411-63-8 ]