6272-25-9|2-Chloro-6-nitroquinoxaline| Ambeed

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Quality Control of [ 6272-25-9 ] Purity: 95% SDS Specification

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Product Details of [ 6272-25-9 ]

CAS No. :	6272-25-9
Formula :	C₈H₄ClN₃O₂
M.W :	209.59
SMILES Code :	C1=C([N+]([O-])=O)C=CC2=C1N=CC(=N2)Cl
MDL No. :	MFCD03067026
InChI Key :	QVWIAHPYYLBQFI-UHFFFAOYSA-N
Pubchem ID :	235714

Safety of [ 6272-25-9 ]

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

Application In Synthesis of [ 6272-25-9 ]

* 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 [ 6272-25-9 ]
Downstream synthetic route of [ 6272-25-9 ]

[ 6272-25-9 ] Synthesis Path-Upstream 1~8

1
[ 25652-34-0 ]
[ 6272-25-9 ]

References: [1] Bioorganic Chemistry, 2014, vol. 56, p. 16 - 26.
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 18, p. 3319 - 3324.
[3] Patent: US2009/264426, 2009, A1, . Location in patent: Page/Page column 43.
[4] Patent: WO2007/29847, 2007, A1, . Location in patent: Page/Page column 66.

2
[ 25652-34-0 ]
[ 6272-25-9 ]

References: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1403 - 1407.
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4508 - 4522.
[3] Patent: WO2007/27532, 2007, A2, . Location in patent: Page/Page column 36-37.

3
[ 1196-57-2 ]
[ 25652-34-0 ]
[ 6272-25-9 ]

References: [1] Patent: US5153196, 1992, A, .

4
[ 1196-57-2 ]
[ 6272-25-9 ]

References: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 18, p. 3319 - 3324.
[2] Bioorganic Chemistry, 2014, vol. 56, p. 16 - 26.

5
[ 6639-87-8 ]
[ 6272-25-9 ]

References: [1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670.

6
[ 95-54-5 ]
[ 6272-25-9 ]

References: [1] Bioorganic Chemistry, 2014, vol. 56, p. 16 - 26.

7
[ 1196-57-2 ]
[ 6272-25-9 ]

References: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 5, p. 1403 - 1407.
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4508 - 4522.

8
[ 109541-15-3 ]
[ 6272-25-9 ]
[ 109541-20-0 ]
[ 109541-21-1 ]

References: [1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670.

[ 6272-25-9 ] Synthesis Path-Downstream 1~35

1
[ 6272-25-9 ]
[ 25652-34-0 ]

References: [1]Justus Liebigs Annalen der Chemie,1953,vol. 579,p. 212,220.

2
[ 110-85-0 ]
[ 6272-25-9 ]
6-nitro-2-piperazin-1-yl-quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 120℃; for 0.166667h;Microwave;	Powered potassium nitrate was added rapidly at 0 0C to a stirred solution of hydroxyquinoxaline (4.38 g, 30 mmol) in 50 mL of concentrated sulfuric acid. After 30 min at 00C, and then room temperature for another 2 h, the mixture was slowly poured into crushed ice at 0 0C (~250 mL). The precipitate was washed with 15 mL of water. Crystallization from acetic acid (200 mL) gave the nitro product as a white solid. To this hydroxy intermediate (502 mg, 2.63 mmol) was added 8 mL of POCl3. The resulting mixture was heated at 1100C for 2 h. The mixture was concentrated by distillation of the solvent. The residue was poured onto ice and basifed with sodium carbonate until pH > 8. The mixture was extracted with ethyl acetate (200 mL x 10). The organic layer was washed with brine, dried with sodium sulfate and concentrated in vacuo to give the nitrochloride product as a dark pink solid. A mixture of this nitrochloride (385 mg, 1.84 mmol), piperazine (600 mg) and 2 mL of ethanol was heated at 120 0C in a microwave for 10 min (Pmax=100 W). The mixture was concentrated and dissolved in DMSO before it was purified by RP-HPLC to give the product as a dark brown oil. Following the same procedure as described in EXAMPLE 21 for the preparation of the urea and the subsequent hydrolysis, the desired nitro product was obtained as a yellow solid. To a solution of this nitro intermediate (20 mg, 0.047 mmol) in 1 mL of DMF/water (10:1) was added tin(II) chloride hydrate (23 mg, 0.12 mmol) at room temperature. The mixture was stirred for 16 h, and then quenched with saturated sodium bicarbonate solution. The mixture was filtered through celite and washed with 30% isopropanol/chloroform. The filtrate was concentrated and purified by Gilson to give the desired product as a reddish brown solid. 1H NMR (acetone-d6, 500 MHz) δ 8.96 (IH, s), 8.64 (IH, d), 8.09 (IH, dd), 7.99 (IH, d), 7.83 (IH, d), 7.72 (IH, dd), 7.58 (IH, t), 7.06 (IH, t), 4.09 (m, 4H), 3.82 (m, 4H); LCMS m/z 393 (M+l).

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 93 - 101.
[2]Patent: WO2007/27532,2007,A2 .Location in patent: Page/Page column 36-37.

3
[ 6272-25-9 ]
[ 115726-26-6 ]

References: [1]Liebigs Annalen der Chemie,1992,p. 899 - 902.

4
[ 6272-25-9 ]
[ 115726-26-6 ]
[ 142396-51-8 ]

References: [1]Liebigs Annalen der Chemie,1992,p. 899 - 902.

5
[ 6272-25-9 ]
[ 143036-89-9 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3319 - 3324.

6
[ 6272-25-9 ]
[ 143007-18-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium azide; In ethanol; water; N,N-dimethyl-formamide;	The <strong>[6272-25-9]2-chloro-6-nitroquinoxaline</strong> (3.00 g, 14.3 mmol), 5 ml of 1 N HCl, and NaN3 (1.12 g, 17.2 mmol) were combined in 60 ml of absolute EtOH, and heated at reflux for 17 hours. A precipitate remained throughout The product was collected by filtration, and air-dried to give 3.8 g of a tan solid. The product was slurried in H2 O and recollected to yield 2.75 g of a light brown solid. Recrystallization from 15 ml of 2:1 DMF/H2 O gave 0.793 g of tan-brown crystals of 7-nitrotetrazolo[1,5-a]quinoxaline (23).

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3319 - 3324.
[2]Patent: US5153196,1992,A .

7
[ 25652-34-0 ]
[ 6272-25-9 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentoxide; trichlorophosphate; at 20℃;Reflux;	Production Example 26-3 2-Chloro-6-nitroquinoxaline At room temperature, phosphorus pentoxide (15.2 g) was added to a phosphorus oxychloride solution (70 mL) of the compound (7.1 g) obtained in Production Example 26-2. The reaction liquid was stirred with heating under reflux for 8 hours, then cooled to room temperature, and poured into water with ice. The formed precipitate was collected by filtration and washed with water. This was dried under reduced pressure to obtain the entitled compound (2.4 g).

References: [1]Bioorganic Chemistry,2014,vol. 56,p. 16 - 26.
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 3319 - 3324.
[3]Patent: US2009/264426,2009,A1 .Location in patent: Page/Page column 43.
[4]Patent: WO2007/29847,2007,A1 .Location in patent: Page/Page column 66.

8
[ 110-91-8 ]
[ 6272-25-9 ]
[ 105866-55-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 0.5h;Heating / reflux;	Into 10. ml of THF was dissolved 1.16 g of <strong>[6272-25-9]2-chloro-6-nitroquinoxaline</strong>, and then 20 ml of morpholine was added thereto, followed by heating under refluxing for 30 minutes. Then, the solvent was removed by evaporation. Water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and saturated saline. After the solvent was removed by evaporation, the residue was crystallized from diethyl ether to obtain 1.5 g of the title compound. FABMASS 261 [M+H]+

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1403 - 1407.
[2]Patent: EP1557411,2005,A1 .Location in patent: Page/Page column 17.

9
[ 109-01-3 ]
[ 6272-25-9 ]
[ 934474-91-6 ]