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Chemistry
Heterocyclic Building Blocks
Quinolines
2,8-Dimethylquinolin-4-ol
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Quinolines
Alcohols

[ CAS No. 15644-80-1 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 15644-80-1
Chemical Structure| 15644-80-1
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Quality Control of [ 15644-80-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 15644-80-1 ]

Product Details of [ 15644-80-1 ]

CAS No. :15644-80-1 MDL No. :MFCD00100264
Formula : C11H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :QUHJYDMHDWSZIP-UHFFFAOYSA-N
M.W :173.21 g/mol Pubchem ID :233217
Synonyms :

Safety of [ 15644-80-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P270-P280-P301+P312-P305+P351+P338-P310-P330-P501 UN#:1759
Hazard Statements:H302-H318 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 15644-80-1 ]

* 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 [ 15644-80-1 ]

[ 15644-80-1 ] Synthesis Path-Downstream   1~39

  • 1
  • [ 50-00-0 ]
  • [ 15644-80-1 ]
  • 5,7-dimethyl-4<i>H</i>-[1,3]dioxino[5,4-<i>c</i>]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
Reference： [1]Monti; Cirelli [Gazzetta Chimica Italiana, 1936, vol. 66, p. 42,45]
  • 2
  • [ 15644-80-1 ]
  • [ 2832-19-1 ]
  • chloro-acetic acid-[(4-hydroxy-2,8-dimethyl-[3]quinolylmethyl)-amide] [ No CAS ]
Reference： [1]Gazzetta Chimica Italiana,1937,vol. 67,p. 621,623
  • 3
  • [ 15644-80-1 ]
  • [ 100-34-5 ]
  • <i>N</i>-(4-hydroxy-2,8-dimethyl-[3]quinolyl)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide Erwaermen mit SnCl2 und konz. wss. HCl und Behandeln mit Acetanhydrid und wss. Natriumacetat;
Reference： [1]Fraser; Tittensor [Journal of the Chemical Society, 1956, p. 1781,1782]
  • 4
  • [ 15644-80-1 ]
  • [ 98-88-4 ]
  • [ 111947-00-3 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride at 160℃;
Reference： [1]Kulkarni et al. [Journal of the Indian Chemical Society, 1951, vol. 28, p. 688,691]
  • 6
  • [ 15644-80-1 ]
  • [ 100-10-7 ]
  • 2-(4-dimethylamino-<i>trans</i>-styryl)-8-methyl-quinolin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol; zinc-chloride-hydroxide; acetic anhydride
Reference： [1]Meyer; Drutel [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 205, p. 462]
  • 7
  • [ 15644-80-1 ]
  • [ 876385-42-1 ]
YieldReaction ConditionsOperation in experiment
With phosphorous (V) sulfide
Reference： [1]Monti; Gallo [Gazzetta Chimica Italiana, 1953, vol. 83, p. 319,322]
  • 8
  • [ 33240-19-6 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; acetic anhydride
Reference： [1]Bangdiwala; Desai [Journal of the Indian Chemical Society, 1953, vol. 30, p. 655]
  • 9
  • [ 141-97-9 ]
  • [ 95-53-4 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
at 20℃; beim Erhitzen des erhaltenen β-o-Tolylimino-buttersaeure-aethylester auf 240grad bis 250grad;
With hydrogenchloride; sulfuric acid; acetic anhydride Multistep reaction;
at 20℃; beim Erhitzen des erhaltenen β-o-Tolylimino-buttersaeure-aethylester auf 240grad bis 250grad;
Reference： [1]Conrad; Limpach [Chemische Berichte, 1888, vol. 21, p. 525]
[2]Desai; Desai, Pratibha; Machhi, Dilip; Desai; Patel, Dinesh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 8, p. 871 - 873]
[3]Current Patent Assignee: Conrad; Limpach - DE42276, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 204][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 204]
  • 10
  • [ 13562-88-4 ]
  • [ 95-53-4 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
With calcium sulfate at 95 - 100℃; Erhitzen des Reaktionsprodukts in Biphenyl und Diphenylaether auf 250grad-260grad;
Reference： [1]Hauser; Reynolds [Journal of the American Chemical Society, 1948, vol. 70, p. 2402]
  • 11
  • [ 15644-80-1 ]
  • [ 89-98-5 ]
  • 2-[(E)-2-(2-Chloro-phenyl)-vinyl]-8-methyl-quinolin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride for 3h; Heating; Yield given;
Reference： [1]Jayabalan, L; Shanmugam, P [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 7, p. 436 - 437]
  • 12
  • [ 15644-80-1 ]
  • [ 79-04-9 ]
  • [ 80820-20-8 ]
YieldReaction ConditionsOperation in experiment
In benzene for 3h; Heating; Yield given;
Reference： [1]Misra; Saxena; Shah [Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1118 - 1119]
  • 13
  • [ 15644-80-1 ]
  • [ 32314-39-9 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate at 75℃;
With trichlorophosphate
With trichlorophosphate at 110℃; for 6h; C Step C: 4-Chloro-2,8-dimethylciuinoline 2,8-Dimethylquinolin-4-ol (0.70 g, 4.0 mmol) was suspended in POC13 (7 mL) and the stirred reaction mixture was heated at 110 °C for 6 h, then cooled to ambienttemperature. The reaction mixture was concentrated to remove most of the POC13 and the residue was poured onto ice with stirring. The resulting mixture was adjusted to pH 7 - 8 by addition of saturated aqueous sodium bicarbonate, and the precipitate was isolated by filtration and dried to give the title compound. MS: m/z = 192.0 (M + 1); 1H NMR (400 MHz, CDC13) ö 8.04 (d, 1H, J 8.4 Hz), 7.58 (d, 1H, J 6.8 Hz), 7.45 (m, 1H), 7.39 (s, 1H), 2.80 (s, 3H), 2.73(s, 3H).
With trichlorophosphate In acetonitrile at 110℃; for 6h; C Step C: 4-Chloro-2,8-dimethylquinoline Step C: 4-Chloro-2,8-dimethylquinoline 2,8-Dimethylquinolin-4-ol (0.70 g, 4.0 mmol) was suspended in POCI3 (7 mL) and the stirred reaction mixture was heated at 110 °C for 6 h, then cooled to ambient temperature. The reaction mixture was concentrated to remove most of the POCI3 and the residue was poured onto ice with stirring. The resulting mixture was adjusted to pH 7 - 8 by addition of saturated aqueous sodium bicarbonate, and the precipitate was isolated by filtration and dried to give the title compound. MS: m/z = 192.0 (M + 1); 1H NMR (400 MHz, CDCi3) δ 8.04 (d, 1H, J = 8.4 Hz), 7.58 (d, 1H, J = 6.8 Hz), 7.45 (m, 1H), 7.39 (s, 1H), 2.80 (s, 3H), 2.73 (s, 3H).
With trichlorophosphate for 3h; Reflux;

Reference： [1]Desai; Desai, Pratibha; Machhi, Dilip; Desai; Patel, Dinesh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 8, p. 871 - 873]
[2]Suresh; Nandha Kumar; Mohan [Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 6, p. 778 - 781]
[3]Current Patent Assignee: MERCK &amp; CO INC - WO2016/22645, 2016, A1 Location in patent: Page/Page column 39
[4]Current Patent Assignee: MERCK &amp; CO INC - WO2016/22644, 2016, A1 Location in patent: Page/Page column 54
[5]Luo, Wei; Liu, Yang; Wang, Jian; Guo, Chun; Lu, Wei-Qiang; Cui, Kun-Qiang [Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3073 - 3079,7]
YieldReaction ConditionsOperation in experiment
o-Toluidin, Acetessigsaeureethylester;
Acetoacet-2-methylanilid, PPA;
o-Toluidin 1. Polyphosphorsaeure, 5 min. 2. Acetessigsaeure-ethylester, 10 min. 3. 140grad, 2 h;
  • 15
  • [ 15644-80-1 ]
  • [ 33513-42-7 ]
  • [ 32314-39-9 ]
  • [ 34550-29-3 ]
  • [ 503552-61-2 ]
YieldReaction ConditionsOperation in experiment
1: 73.5% 2: 18% 3: 5% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1.5h; Stage #2: 2,8-dimethyl-quinolin-4-ol at 100℃; for 12.5h;
1: 73.5% 2: 18% 3: 5% Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 1h; cooling; Stage #2: 2,8-dimethyl-quinolin-4-ol for 12.5h; Heating;
Reference： [1]Nandha Kumar; Suresh; Mohan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 9, p. 2069 - 2073]
[2]Kumar, R. Nandha; Suresh; Dhanabal; Mohan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 4, p. 846 - 851]
  • 16
  • 3-<i>o</i>-tolylamino-but-2-enoic acid ethyl ester [ No CAS ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
In diphenylether at 240℃;
In diphenylether at 240℃;
Reference： [1]Nandha Kumar; Suresh; Mohan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 9, p. 2069 - 2073]
[2]Nandhakumar; Suresh; Jude, A.L. Calistus; Rajesh kannan; Mohan [European Journal of Medicinal Chemistry, 2007, vol. 42, # 8, p. 1128 - 1136]
  • 17
  • [ 15644-80-1 ]
  • [ 33513-42-7 ]
  • [ 32314-39-9 ]
  • [ 34550-29-3 ]
  • 4-chloro-3-formyl-8-methyl-2-(2-hydroxyethen-1-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 73.5% 2: 18% 3: 5% With trichlorophosphate for 12.5h; Heating;
1: 73.5% 2: 18% 3: 5% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; for 1h; Stage #2: 2,8-dimethyl-quinolin-4-ol at 100℃; for 15h; Further stages.;
1: 73.5% 2: 18% 3: 5% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 5℃; Stage #2: 2,8-dimethyl-quinolin-4-ol at 100℃; for 12.5h; Stage #3: With water cooling; Further stages.;
Reference： [1]Kumar, Nandha; Suresh; Dhanabal; Mohan [Journal of the Indian Chemical Society, 2004, vol. 81, # 7, p. 598 - 601]
[2]Nandhakumar; Suresh; Jude, A.L. Calistus; Rajesh kannan; Mohan [European Journal of Medicinal Chemistry, 2007, vol. 42, # 8, p. 1128 - 1136]
[3]Kumar, R. Nandha; Suresh; Dhanabal; Mohan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2007, vol. 46, # 6, p. 995 - 1000]
  • 18
  • [ 15644-80-1 ]
  • [ 870620-99-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: POCl3 2: 86 percent / ethanol / 6.5 h / Heating
Reference： [1]Suresh; Nandha Kumar; Mohan [Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 6, p. 778 - 781]
  • 19
  • [ 15644-80-1 ]
  • 4,6-dimethyl-5,8,12-triaza-benzo[<i>a</i>]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: POCl3 2: 86 percent / ethanol / 6.5 h / Heating 3: 73 percent / POCl3 / 16 h / Heating
Reference： [1]Suresh; Nandha Kumar; Mohan [Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 6, p. 778 - 781]
  • 20
  • [ 95-53-4 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. HCl / 20 °C 2: diphenyl ether / 240 °C
Reference： [1]Nandha Kumar; Suresh; Mohan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 9, p. 2069 - 2073]
  • 21
  • [ 15644-80-1 ]
  • N-Diaminomethylene-4-(2,8-dimethyl-quinolin-4-ylamino)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorous oxychloride / 75 °C 2: Heating; 4-16 h
Reference： [1]Desai; Desai, Pratibha; Machhi, Dilip; Desai; Patel, Dinesh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 8, p. 871 - 873]
  • 22
  • [ 15644-80-1 ]
  • N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(2,8-dimethyl-quinolin-4-ylamino)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorous oxychloride / 75 °C 2: Heating; 4-16 h
Reference： [1]Desai; Desai, Pratibha; Machhi, Dilip; Desai; Patel, Dinesh [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 8, p. 871 - 873]
  • 23
  • [ 15644-80-1 ]
  • (5-Phenylamino-[1,3,4]thiadiazol-2-ylsulfanyl)-acetic acid 2,8-dimethyl-quinolin-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / 3 h / Heating 2: Na2CO3 / H2O; dimethylformamide / 3 h / Heating
Reference： [1]Misra; Saxena; Shah [Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1118 - 1119]
  • 24
  • [ 15644-80-1 ]
  • (5-p-Tolylamino-[1,3,4]thiadiazol-2-ylsulfanyl)-acetic acid 2,8-dimethyl-quinolin-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / 3 h / Heating 2: Na2CO3 / H2O; dimethylformamide / 3 h / Heating
Reference： [1]Misra; Saxena; Shah [Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1118 - 1119]
  • 25
  • [ 15644-80-1 ]
  • [5-(4-Chloro-phenylamino)-[1,3,4]thiadiazol-2-ylsulfanyl]-acetic acid 2,8-dimethyl-quinolin-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / 3 h / Heating 2: Na2CO3 / H2O; dimethylformamide / 3 h / Heating
Reference： [1]Misra; Saxena; Shah [Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1118 - 1119]
  • 26
  • [ 15644-80-1 ]
  • [5-(4-Methoxy-phenylamino)-[1,3,4]thiadiazol-2-ylsulfanyl]-acetic acid 2,8-dimethyl-quinolin-4-yl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene / 3 h / Heating 2: Na2CO3 / H2O; dimethylformamide / 3 h / Heating
Reference： [1]Misra; Saxena; Shah [Journal of the Indian Chemical Society, 1981, vol. 58, # 11, p. 1118 - 1119]
  • 27
  • [ 15644-80-1 ]
  • 4,12-Dichloro-8-methyl-benzo[a]acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Ac2O / 3 h / Heating 2: I2 / benzene; methanol / 15 h / Irradiation 3: POCl3 / 2 h / Heating
Reference： [1]Jayabalan, L; Shanmugam, P [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 7, p. 436 - 437]
  • 28
  • [ 15644-80-1 ]
  • [ 143287-49-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Ac2O / 3 h / Heating 2: I2 / benzene; methanol / 15 h / Irradiation
Reference： [1]Jayabalan, L; Shanmugam, P [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 7, p. 436 - 437]
  • 29
  • [ 15644-80-1 ]
  • 3-aminomethyl-2,8-dimethyl-quinolin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: concentrated H2SO4 2: aqueous HCl
Reference： [1]Monti [Gazzetta Chimica Italiana, 1937, vol. 67, p. 621,623]
  • 30
  • [ 15644-80-1 ]
  • bis-(2,8-dimethyl-[4]quinolylmercapto)-methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: phosphorus (V)-sulfide 2: sodium ethylate; ethanol / anschliessenden Erwaermen mit Dichlormethan
Reference： [1]Monti; Gallo [Gazzetta Chimica Italiana, 1953, vol. 83, p. 319,322]
  • 31
  • [ 105-45-3 ]
  • [ 95-53-4 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
tert-butyl (3S,4S)-4-({4-[(2,8-dimethyl-4-quinolinyl)methyl]benzoyl}amino)-3-[(hydroxyamino)carbonyl]-1-pyrrolidinecarboxylate tert-butyl (3S,4S)-4-({4-[(2,8-dimethyl-4-quinolinyl)methyl]benzoyl}amino)-3-[(hydroxyamino)carbonyl]-1-pyrrolidinecarboxylate (456a) Following a procedure similar to (454a), 2-methylaniline (21.4 g, 0.2 mol) was condensed with methyl acetoacetate (23.2 g, 0.2 mol) to provide the desired 2,8-dimethyl-4-hydroxyquinoline (456a) (13.0 g, 38%). MS (AP+): 173 (M+1). (456b) Following a procedure similar to (434a), the product from (456a) (10.0 g, 58.4 mmol) was converted to the corresponding bromide (456b) (11.0 g, 80%). MS (AP+): 236 (M+1). (456c) Following a similar procedure of (401b), the product from (456b) (9.6 g, 41 mmol) was converted to the corresponding product (456c) (9.0 g, 69%). MS (ES+): 322 (M+1).
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2003/139388, 2003, A1
  • 32
  • [ 15644-80-1 ]
  • [ 1263193-27-6 ]
YieldReaction ConditionsOperation in experiment
With hydrazine dihydrochloride; hydrazine hydrate In ethylene glycol at 200℃; 4.1.1. General procedure I. Synthesis of 2-(3-methyl-1H-pyrazol-5-yl)anilines 3a-i General procedure: A mixture of 2-methyl-4-quinolinol 2 (1 equiv, 6.28 mmol), hydrazine dihydrochloride (1 equiv, 6.28 mmol), 99% hydrazine monohydrate (10 equiv, 62.8 mmol) in ethylene glycol (5 ml) was slowly heated to 200 °C and stirred for 5 h at the same temperature. The mixture was then poured onto H2O (15 ml) and stirred at room temperature for 2 h. The desired compounds were isolated as below indicated.
Reference： [1]Location in patent: experimental part Asproni, Battistina; Murineddu, Gabriele; Pau, Amedeo; Pinna, Gérard A.; Langgård, Morten; Christoffersen, Claus Tornby; Nielsen, Jacob; Kehler, Jan [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 642 - 649]
  • 33
  • [ 15644-80-1 ]
  • 4-chloro-8-methyl-2-(1-phenyl-1H-pyrazol-4-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 1 h / 10 - 20 °C / Inert atmosphere 1.2: pH 6 - 6.5 / Inert atmosphere; Cooling with ice 2.1: acetic acid / 24 h / 20 °C / Inert atmosphere
Reference： [1]Aleksanyan, Iskuhi; Sargsyan, Karine; Panosyan, Henrik [Heterocyclic Communications, 2011, vol. 17, # 3-4, p. 105 - 110]
  • 34
  • [ 15644-80-1 ]
  • 8-methyl-2-(1-phenyl-1H-pyrazol-4-yl)-4-piperidinoquinoline hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 1 h / 10 - 20 °C / Inert atmosphere 1.2: pH 6 - 6.5 / Inert atmosphere; Cooling with ice 2.1: ethanol / Inert atmosphere 3.1: acetic acid / 24 h / 20 °C / Inert atmosphere 3.2: pH 1 / Inert atmosphere; Cooling with ice
Reference： [1]Aleksanyan, Iskuhi; Sargsyan, Karine; Panosyan, Henrik [Heterocyclic Communications, 2011, vol. 17, # 3-4, p. 105 - 110]
  • 35
  • [ 15644-80-1 ]
  • [ 33513-42-7 ]
  • 2-(4-chloro-8-methylquinolin-2-yl)-3-hydroxyacrylaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 2,8-dimethyl-quinolin-4-ol; N,N-dimethyl-formamide With trichlorophosphate at 10 - 20℃; for 1h; Inert atmosphere; Stage #2: With water; sodium hydroxide Inert atmosphere; Cooling with ice;
Reference： [1]Location in patent: experimental part Aleksanyan, Iskuhi; Sargsyan, Karine; Panosyan, Henrik [Heterocyclic Communications, 2011, vol. 17, # 3-4, p. 105 - 110]
  • 36
  • [ 33240-19-6 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
In diphenylether at 250℃; for 1h; B Step B: 2,8-Dimethylcuinolin-4-ol A stirred solution of ethyl 3-[(2-methylphenyl)amino]but-2-enoate (2.0 g, 9.1 mmol) in diphenyl ether (20 mL) was heated at 250 °C for 1 h, then cooled to ambient temperature. The resulting precipitate was isolated by filtration, washing with petroleum ether,and dried to give the title compound.
In diphenylether at 250℃; for 1h; B Step B: 2,8-Dimethylquinolin-4-ol Step B: 2,8-Dimethylquinolin-4-ol A stirred solution of ethyl 3-[(2-methylphenyl)amino]but-2-enoate (2.0 g, 9.1 mmol) in diphenyl ether (20 mL) was heated at 250 °C for 1 h, then cooled to ambient temperature. The resulting precipitate was isolated by filtration, washing with petroleum ether, and dried to give the title compound.
In diphenylether for 0.5h; Reflux;
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2016/22645, 2016, A1 Location in patent: Page/Page column 39
[2]Current Patent Assignee: MERCK & CO INC - WO2016/22644, 2016, A1 Location in patent: Page/Page column 54
[3]Luo, Wei; Liu, Yang; Wang, Jian; Guo, Chun; Lu, Wei-Qiang; Cui, Kun-Qiang [Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3073 - 3079,7]
  • 37
  • [ 15644-80-1 ]
  • [ 49612-06-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate / 3 h / Reflux 2: hydrazine hydrate / Reflux
Reference： [1]Luo, Wei; Liu, Yang; Wang, Jian; Guo, Chun; Lu, Wei-Qiang; Cui, Kun-Qiang [Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3073 - 3079,7]
  • 38
  • [ 15644-80-1 ]
  • [ 1350539-04-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 3 h / Reflux 2: hydrazine hydrate / Reflux 3: acetic acid / methanol / 7 h / 20 °C
Reference： [1]Luo, Wei; Liu, Yang; Wang, Jian; Guo, Chun; Lu, Wei-Qiang; Cui, Kun-Qiang [Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3073 - 3079,7]
  • 39
  • [ 95-53-4 ]
  • [ 15644-80-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 16 h / Reflux 2: diphenylether / 1 h / 250 °C
Multi-step reaction with 2 steps 1: methanol / 7 h / 40 °C 2: diphenylether / 0.5 h / Reflux
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2016/22645, 2016, A1 Current Patent Assignee: MERCK & CO INC - WO2016/22644, 2016, A1
[2]Luo, Wei; Liu, Yang; Wang, Jian; Guo, Chun; Lu, Wei-Qiang; Cui, Kun-Qiang [Medicinal Chemistry Research, 2012, vol. 21, # 10, p. 3073 - 3079,7]

Tags: 15644-80-1 synthesis path| 15644-80-1 SDS| 15644-80-1 COA| 15644-80-1 purity| 15644-80-1 application| 15644-80-1 NMR| 15644-80-1 COA| 15644-80-1 structure

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