30465-68-0|5-Methoxyquinolin-8-amine| Ambeed

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Quality Control of [ 30465-68-0 ] Purity: 97% SDS Specification

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Product Details of [ 30465-68-0 ]

CAS No. :	30465-68-0
Formula :	C₁₀H₁₀N₂O
M.W :	174.20
SMILES Code :	NC1=C2N=CC=CC2=C(OC)C=C1
MDL No. :	MFCD01593679
InChI Key :	MFLLTRMMFHENCM-UHFFFAOYSA-N
Pubchem ID :	777110

Safety of [ 30465-68-0 ]

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

Application In Synthesis of [ 30465-68-0 ]

* 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 [ 30465-68-0 ]

[ 30465-68-0 ] Synthesis Path-Downstream 1~36

1
[ 30465-68-0 ]
[ 869-24-9 ]
[ 47054-90-0 ]

References: [1]Journal of the American Chemical Society,1946,vol. 68,p. 1524,1526.

2
[ 36020-53-8 ]
[ 30465-68-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium on activated charcoal; hydrogen; In ethanol; at 20℃; for 6h;Inert atmosphere;	first, 5-methoxy-8-nitroquinoline (0.4 g, 2.33 mmol) was added to a two-neck eggplant flask and the mixture was made under nitrogen, and 50 ml of dehydrated ethanol was added to it. Palladium on carbon (0.04 g) was added under hydrogen and stirred at ambient temperature. After 6 hours, filtration was carried out using Celite, and the filtrate was concentrated with an evaporator to obtain a yellow solid was 0.333 g in a yield of 83%
53%	With tin(II) chloride dihdyrate; In ethanol;Reflux;	3. Synthesis of 5-methoxy-quinolin-8-ylamine (45); A suspension of 5-methoxy-8-nitroquinoline 44 (5.8 g, 28.5 mmol) and SnCI2.2H2O (19.3 g, 85.6 mmol) in ethanol (120 ml_) was heated to reflux for 1 hour. The reaction mixture was diluted with ethyl acetate and treated with 10% NaOH up to pH 11. The organic layer was separated, washed with brine, dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography (SiO2, ethyl acetate/hexane, 0-40%) to obtain the final amine 45 (2.7 g, 53%) as a brown solid. 1H-NMR (400 MHz, CDCI3, ppm): 8.79 (H-2, dd, 1 H, J=1.7 and 4.2 Hz), 8.51 (H-4, dd, 1 H, J=1.7 and 8.5 Hz), 7.38 (H-3, dd, 1 H, J=4.2 and 8.5 Hz), 6.89 (H-7, d, 1 H, J=8.2 Hz), 6.73 (H-6, d, 1 H, J=8.2 Hz), 3.95 (OCH3, s, 3H).

References: [1]Dalton Transactions,2019,vol. 48,p. 13205 - 13211.
[2]Chemistry - A European Journal,2013,vol. 19,p. 14697 - 14701.
[3]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1679 - 1688.
[4]Patent: JP5659191,2015,B2 .Location in patent: Paragraph 0081; 0082; 0083; 0084.
[5]Patent: WO2010/66832,2010,A1 .Location in patent: Page/Page column 31-32.
[6]Journal of the American Chemical Society,1946,vol. 68,p. 1524,1526.
[7]Organic Letters,2014,vol. 16,p. 4956 - 4959.
[8]Chemical Communications,2016,vol. 52,p. 6423 - 6426.
[9]Chemistry - A European Journal,2017,vol. 23,p. 14450 - 14453.

3
[ 30465-68-0 ]
[ 79-10-7 ]
3-(5-methoxy-quinolin-8-ylamino)-propionic acid [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,2000,vol. 36,p. 432 - 438.

4
[ 30465-68-0 ]
molybdenyl chloride etherate [ No CAS ]
[ 113054-37-8 ]

References: [1]Koordinatsionnaya Khimiya,1987,vol. 13,p. 703 - 711.
Koordinatsionnaya Khimiya,1987,vol. 13,p. 1232 - 1239.

5
[ 30465-68-0 ]
[ 762-42-5 ]
[ 1228760-47-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	In methanol; at 4 - 20℃;	4. Synthesis of 2-(5-methoxyquinolin-8-ylamino)-but-2-enedioic acid dimethyl ester (46); To a solution of 5-methoxyquinolin-8-ylannine 45 (2.7 g, 15.3 mmol) in methanol (20 ml_) at 40C, dimethylacetylenedicarboxylate (2.1 ml_, 16.8 mmol) was added. The reaction mixture was stirred and allowed to warm to room temperature for 3 hours. The solvent was evaporated and the residue was washed with MeOH and hexane, yielding an orange solid that was dried under vacuum (3.8 g, 79%).1H-NMR (400 MHz, CDCI3, ppm): 10.63 (NH, s, 1 H), 8.90 (H-2, dd, 1 H, J=1.7 and 4.2 Hz), 8.53 (H-4, dd, 1 H, J=1.7 and 8.4 Hz), 7.41 (H-3, dd, 1 H, J=4.2 and 8.4 Hz), 6.95 (H-7, d, 1 H, J=8.3 Hz), 6.73 (H-6, d, 1 H, J=8.3Hz), 5.44 (s, 1 H, CH=), 3.96 (OCH3, s, 3H), 3.77 (CO2CH3, s, 3H), 3.69 (CO2CH3, s, 3H).

References: [1]Patent: WO2010/66832,2010,A1 .Location in patent: Page/Page column 32.

6
[ 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.

8
[ 30465-68-0 ]
2-[bis(pyridin-2-ylmethyl)]amino-N-(5-methoxyquinolin-8-yl)acetamide [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14697 - 14701.
[2]Patent: JP5659191,2015,B2 .
[3]Dalton Transactions,2019,vol. 48,p. 13205 - 13211.

9
[ 30465-68-0 ]
[ 598-21-0 ]
2-bromo-N-(5-methoxyquinolin-8-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In acetonitrile; at 0℃; for 3.16h;Inert atmosphere;	first, sodium carbonate (0.285 g, 2.7 mmol) and 5 - methoxy - 8 - aminoquinoline (0.33 g, 1.91 mmol) were placed in a reaction vessel and the atmosphere was brought to an argon atmosphere, 5 mL of dehydrated acetonitrile was added. After bringing the reaction vessel to 0 C. in an ice bath, bromoacetyl bromide (0.2 mL, 2.3 mmol) was added over 10 minutes with stirring. After 3 hours, the white precipitate was removed by suction filtration using celite, the filtrate was concentrated by an evaporator and then dried under vacuum.

References: [1]Dalton Transactions,2019,vol. 48,p. 13205 - 13211.
[2]Chemistry - A European Journal,2013,vol. 19,p. 14697 - 14701.
[3]Patent: JP5659191,2015,B2 .Location in patent: Paragraph 0085; 0086; 0087.

10
[ 30465-68-0 ]
[ 5511-73-9 ]
(S)-2-(1,3-dioxoisoindolin-2-yl)-N-(5-methoxyquinolin-8-yl)-3-methylbutanamide [ No CAS ]