67074-63-9|4-Methyl-3,4-dihydroquinoxalin-2(1H)-one| Ambeed

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Quality Control of [ 67074-63-9 ] Purity: 97% SDS Specification

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Product Details of [ 67074-63-9 ]

CAS No. :	67074-63-9
Formula :	C₉H₁₀N₂O
M.W :	162.19
SMILES Code :	O=C1NC2=C(C=CC=C2)N(C)C1
MDL No. :	MFCD13152341
InChI Key :	HRTXKMRWMTUZDZ-UHFFFAOYSA-N
Pubchem ID :	12938663

Safety of [ 67074-63-9 ]

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

Application In Synthesis of [ 67074-63-9 ]

* 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 [ 67074-63-9 ]

[ 67074-63-9 ] Synthesis Path-Downstream 1~24

1
[ 105-36-2 ]
[ 67074-63-9 ]
[ 120589-82-4 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1475 - 1479.

2
[ 59564-59-9 ]
[ 80-48-8 ]
[ 67074-63-9 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1475 - 1479.

3
[ 140-18-1 ]
[ 67074-63-9 ]
[ 120589-83-5 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1475 - 1479.

6
1,1-dimethyl-3-oxo-1,2,3,4-tetrahydroquinoxalinium chloride [ No CAS ]
[ 67074-63-9 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 790 - 802.

7
[methyl-(2-nitro-phenyl)-amino]-acetic acid methyl ester [ No CAS ]
[ 67074-63-9 ]

References: [1]European Journal of Organic Chemistry,2003,p. 2314 - 2326.

8
[ 2836-03-5 ]
[ 67074-63-9 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 790 - 802.

9
[ 714194-84-0 ]
[ 67074-63-9 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 790 - 802.

10
[ 610-17-3 ]
[ 67074-63-9 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 790 - 802.

11
[ 67074-63-9 ]
[ 120589-84-6 ]

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1475 - 1479.

12
[ 67074-63-9 ]
[ 3476-89-9 ]

Yield	Reaction Conditions	Operation in experiment
95%		24c. 1,2,3,4-tetrahydroquinoxaline To a solution of 24b (300 mg, 1.85 mmol) in THF (2 mL) was added 1N LiAlH4 (10 mL, 10 mmol). The reaction mixture was stirred at rt for 1 h. The reaction mixture was quenched with H2O (1 mL) at 0 C., 15% NaOH (1 mL), followed by H2O (1 mL). The reaction mixture was extracted with EtOAc. The EtOAc was then washed with brine, dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 24c (260 mg, 95%) as white powder. LC-MS ESI m/z 149 [M+H]+.

References: [1]Patent: US2005/261244,2005,A1 .Location in patent: Page/Page column 53.

13
[ 50-00-0 ]
[ 59564-59-9 ]
[ 67074-63-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; sodium cyanoborohydride; acetic acid; In methanol; water; at 20 - 50℃; for 9h;	24b. 4-methyl-3,4-dihydroquinoxalin-2(1H)-one To a solution of 24a (500 mg, 3.378 mmol) in MeOH (3 mL) was added NaBH3CN (425 mg, 6.76 mmol), paraformaldehyde (102 mg), followed by HOAc (30 muL). The reaction mixture was stirred at rt for 4 h. Another portion of NaBH4CN (212 mg, 3.37 mmol) and parafornaldehyde (51 mg) were added to the reaction mixture along with conc. HCl (10 muL). The reaction mixture was stirred at 50 C. for 5 h and cooled to rt. The pH was adjusted to 8 and the solvent was evaporated under reduced pressure. The desired product was extracted into EtOAc and washed it with brine, dried over Na2SO4. The solvent was evaporated under reduced pressure to afford 24b (537 mg, 98%) as beige powder. LC-MS ESI m/z 163 [M+H]+.
94.5%		A solution of 3,4-dihydroquinoxalin-2-(1H)-one (2.9 g, 19.6 mmol) in methanol (20 mL) Sodium cyanoborohydride (2.5 g, 39.7 mmol) was added, Paraformaldehyde (0.9 g) and glacial acetic acid (1 mL) The reaction was stirred at 25 C for 4 hours, Sodium cyanoborohydride (1.2 g, 19.0 mmol) was added, Paraformaldehyde (0.45 g) and hydrochloric acid (0.5 mL), The reaction was heated to 50 C for 5 hours. The reaction solution was cooled to room temperature, The pH was adjusted to 8 with saturated aqueous sodium bicarbonate solution, Ethyl acetate (50 mL x 3) was added, Combine organic phase, Dried over anhydrous sodium sulfate, filter, concentrate, To give the title compound (3.0 g, yield 94.5%).

References: [1]Patent: US2005/261244,2005,A1 .Location in patent: Page/Page column 53.
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 9275 - 9295.
[3]Patent: CN106317027,2017,A .Location in patent: Paragraph 0196; 0197; 0198.

14
[ 1049772-54-4 ]
[ 67074-63-9 ]

References: [1]Organic Letters,2010,vol. 12,p. 3574 - 3577.

15
[ 95-54-5 ]
[ 67074-63-9 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9275 - 9295.
[2]Patent: CN106317027,2017,A .

16
[ 67074-63-9 ]
1-(2-(4-methyl-3,4-dihydroquinoxalin-1(2H)-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9275 - 9295.

17
[ 67074-63-9 ]
[ 870072-68-7 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9275 - 9295.

18
[ 67074-63-9 ]
[ 870072-69-8 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9275 - 9295.

19
[ 67074-63-9 ]
[ 36438-97-8 ]

Yield	Reaction Conditions	Operation in experiment
91.3%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 25℃; for 1h;	A solution of 4-methyl-3,4-dihydroquinoxalin-2-(1H) -one (3.0 g, 18.5 mmol) in tetrahydrofuran (50 mL) Cooled to 0 C, lithium aluminum hydride (2.1 g, 55.3 mmol) was added in portions, The reaction was continued slowly to 25 C for 1 hour. The reaction solution was quenched with water (50 mL) ethyl acetate (30 mL x 3) was added, Combine organic phase, Dried over anhydrous sodium sulfate, filter, concentrate, The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) To give the title compound (2.5 g, yield 91.3%).

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9275 - 9295.
[2]Patent: CN106317027,2017,A .Location in patent: Paragraph 0199; 000; 0201.

20
[ 67074-63-9 ]
(2-((2,5-dichlorophenyl)amino)pyridin-3-yl)-(4-methyl-3,4-dihydroquinoxaline-1-(2H)-yl)methanone [ No CAS ]