14208-35-6|1-(2-Methylquinolin-3-yl)ethanone| Ambeed

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Quality Control of [ 14208-35-6 ] Purity: 95% SDS Specification

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Product Details of [ 14208-35-6 ]

CAS No. :	14208-35-6
Formula :	C₁₂H₁₁NO
M.W :	185.22
SMILES Code :	CC(C1=CC2=CC=CC=C2N=C1C)=O
MDL No. :	MFCD09754368
InChI Key :	OKDWGFQXJYJNIJ-UHFFFAOYSA-N
Pubchem ID :	4729271

Safety of [ 14208-35-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 14208-35-6 ]

* 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 [ 14208-35-6 ]

[ 14208-35-6 ] Synthesis Path-Downstream 1~35

1
[ 110-89-4 ]
[ 64-17-5 ]
[ 529-23-7 ]
[ 123-54-6 ]
[ 14208-35-6 ]

References: [1]Chemische Berichte,1907,vol. 40,p. 3433.

2
[ 14208-35-6 ]
[ 529-23-7 ]
3-(2-amino-phenyl)-1-(2-methyl-[3]quinolyl)-propenone [ No CAS ]

References: [1]Annali di Chimica,1953,vol. 43,p. 242,245.

3
[ 106380-95-4 ]
[ 14208-35-6 ]

References: [1]Tetrahedron,1959,vol. 6,p. 97,102.

4
[ 529-23-7 ]
[ 123-54-6 ]
[ 14208-35-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With Nafion NR50; In ethanol; at 200℃; for 1.0h;Microwave irradiation;	General procedure: A mixture of 2-aminobenzophenone 2 (1.0 mmol), ketone 3 or 4 (1.1 mmol), and Nafion NR50 (20 mol%) in ethanol (10 mL) was loaded into a dried 35 mL microwave vial at 25 C. The mixture was subjected to microwave irradiation and stirred at 200 C for 1 h. Consumption of the starting materials was confirmed by TLC. The mixture was cooled to 25 C and then transferred to a 100 mL round-bottom flask; the solvent was concentrated under reduced pressure to afford crude product. The solid crude product was recrystallized (hexane-EtOAc, 5:1 to 2:1). The oily or gummy crude product was purified by column chromatography (silica gel, hexanes-EtOAc, 4:1 to 1:1). This afforded products 1a-ac, 5a-k, and 6a-p.
64%	With magnesium(II) chloride hexahydrate; In ethanol; at 80℃; for 12.0h;Schlenk technique;	General procedure: A mixture of 2-aminoaryl ketones 1 (0.50 mmol), β-ketoesters/ketones 2 (1.0 mmol), and magnesium chloride (MgCl2 · 6H2O, 20.3 mg, 0.10 mmol) in EtOH (3 mL) was added into a Schlenk flask (25 mL) and the mixture was stirred at 80 C until the reaction was finished. Then the solvent was evaporated under reduced pressure and the residue was purified by column chromatography.
51%	In water; for 5.0h;Reflux;	To compound 6-1 (1.0 g, 8.25 mmol) dissolved in water (20 mL) was added acetylacetone (826 mg, 8.25 mmol) and reacted at reflux for 5 h. When the completion of the reaction was monitored by LC-MS, the reaction solution was poured into ice water, then extracted with ethyl acetate. The organic phases were combined, washed once with saturated aqueous salt solution, dried with sodium sulfate, filtered and concentrated, and purified by column chromatography to obtain the target product 6-2 (780 mg) with a yield of 51%.

References: [1]Journal of Heterocyclic Chemistry,2020,vol. 57,p. 132 - 139.
[2]Synthesis,2020,vol. 52,p. 1779 - 1794.
[3]Synthesis,2012,vol. 44,p. 389 - 392.
[4]Synthetic Communications,2018,vol. 48,p. 830 - 837.
[5]Patent: US2020/239429,2020,A1 .Location in patent: Paragraph 0141-0142.
[6]European Journal of Organic Chemistry,2017,vol. 2017,p. 6375 - 6381.
[7]Chemische Berichte,1892,vol. 25,p. 1757.
[8]Chemische Berichte,1907,vol. 40,p. 3433.
[9]Pharmaceutical Bulletin,1955,vol. 3,p. 21,24.
[10]Justus Liebigs Annalen der Chemie,1943,vol. 554,p. 269,284.

5
[ 55857-35-7 ]
[ 123-54-6 ]
[ 14208-35-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1943,vol. 554,p. 269,284.

6
3-(2-azidobenzylidene)-pentane-2,4-dione [ No CAS ]
[ 14208-35-6 ]

Yield	Reaction Conditions	Operation in experiment
30%	In water; acetic acid; at 20 - 25℃; for 6.0h;Irradiation; Inert atmosphere;	General procedure: In a quartz tube under argon were successively added ortho-azidocinnamoyl derivative 1akand the appropriate solvent, with [1] = 3.2 mM. The resulting mixture was then irradiatedusing either the LUMOS 43 (1.5 h stirring time) or a conventional Tungsten lamp (6 hstirring time), as light sources. After evaporation of the solvent, purification of the crude bycolumn chromatography, eluting with an appropriate CY / EtOAc mixture, furnished thedesired photocyclized products 2a-k or 3/4 in pure forms.

References: [1]Tetrahedron Letters,1990,vol. 31,p. 6561 - 6564.
[2]Journal of Organic Chemistry,2019,vol. 84,p. 12031 - 12039.
[3]Synlett,2017,vol. 28,p. 2614 - 2618.
[4]Synthetic Communications,2015,vol. 45,p. 2802 - 2809.

7
[ 14208-35-6 ]
2-methyl-3-(1-hydroxyethyl)quinoline [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 1189 - 1195.

8
[ 14208-35-6 ]
1-(2-Methyl-1,2,3,4-tetrahydro-quinolin-3-yl)-ethanone [ No CAS ]
1-(2-Methyl-1,2-dihydro-quinolin-3-yl)-ethanone [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 1189 - 1195.

10
[ 7732-18-5 ]
[ 529-23-7 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 123-54-6 ]
[ 14208-35-6 ]

References: [1]Chemische Berichte,1892,vol. 25,p. 1757.

11
[ 815-68-9 ]
[ 529-23-7 ]
[ 14208-35-6 ]

References: [1]Heterocycles,2005,vol. 65,p. 2777 - 2782.

12
[ 91-56-5 ]
[ 14208-35-6 ]

References: [1]Tetrahedron,1959,vol. 6,p. 97,102.

13
[ 123-54-6 ]
[ 14208-35-6 ]

References: [1]Tetrahedron,1959,vol. 6,p. 97,102.
[2]Tetrahedron,1959,vol. 6,p. 97,102.
[3]Synthetic Communications,2015,vol. 45,p. 2802 - 2809.

14
[ 123-54-6 ]
[ 55857-35-7 ]
[ 14208-35-6 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 5715 - 5718.

15
[ 27669-22-3 ]
[ 14208-35-6 ]

References: [1]Synthesis,2011,p. 2066 - 2072.

16
[ 123-54-6 ]
[ 552-89-6 ]
[ 14208-35-6 ]

References: [1]RSC Advances,2014,vol. 4,p. 37806 - 37811.
[2]Synthesis,2011,p. 2066 - 2072.

17
ortho-azido-β-nitrostyrene [ No CAS ]
[ 123-54-6 ]
[ 14208-35-6 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: To an oven-dried, 25 mL round-bottom flask equipped with a magnetic bar was added ortho-azido-β-nitro-styrene 1 (0.5 mmol, 1.0 equiv), ethyl acetoacetate 2a (0.6 mmol, 1.2 equiv), L-proline (0.1 mmol, 20 mol %) and NEt3 (0.5 mmol, 1.0 equiv) in anhydrous CH2Cl2 (2 mL) at room temperature. The resulting mixture was then allowed to be stirred for 2 h till the reaction completed (monitored by TLC). Ph3P (131 mg, 0.5 mmol, 1.0 equiv) was added, and the mixture was stirred for another 3-5 h. The solid formed was filtered off, after the filtrate was concentrated under reduced pressure, the residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc=4:1). 4.2.3. 1-(2-Methyl-3-quinolyl) ethanone (3c). The title compound was prepared according to the procedure for 3a. The product was obtained as pale yellow crystals (85.1 mg, 92% yield, mp 77-78 C; [Lit. 79-80 C]); 1H NMR (400 MHz, CDCl3): δ=8.50 (s, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.87 (d, J=8.0 Hz, 1H), 7.80 (t, J=8.0 Hz, 1H), 7.57 (t, J=8.0 Hz, 1H), 2.92 (s, 3H), 2.74 (s, 3H); 13C NMR (100 MHz, CDCl3): δ=199.9, 157.6, 148.1, 138.3, 131.7, 130.9, 128.4, 128.3, 126.6, 125.5, 29.1, 25.6.

References: [1]Tetrahedron,2013,vol. 69,p. 8137 - 8141.

18
[ 5344-90-1 ]
[ 123-54-6 ]
[ 14208-35-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With manganese(IV) oxide; In ethanol;Reflux;	General procedure: To a clear solution of 2-amino benzyl alcohol or 6-chloro benzyl alcohol 1 (1mmol) in EtOH containing MnO2 (3mmol), compound 2(a-c) (1mmol) was added and the reaction mixture was refluxed for appropriate time (TLC control). The reaction mixture was filtered through celite bed. From the filtrate, ethanol was removed under reduced pressure and residue was subjected to column chromatography to obtain pure product 3(a-c).

References: [1]European Journal of Medicinal Chemistry,2013,vol. 70,p. 536 - 547.
[2]RSC Advances,2016,vol. 6,p. 31386 - 31390.

19
[ 14208-35-6 ]
[ 93-02-7 ]
C₂₁H₁₉NO₃ [ No CAS ]