[ CAS No. 6270-08-2 ] {[proInfo.proName]}

Name: 6270-08-2|4-Chloro-2,6-dimethylquinoline|97%
Brand: Ambeed
SKU: A758902
Rating: 98 (26 reviews)

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Quality Control of [ 6270-08-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6270-08-2 ]

SDS Specification

Alternatived Products of [ 6270-08-2 ]

Product Details of [ 6270-08-2 ]

CAS No. :	6270-08-2	MDL No. :	MFCD00272394
Formula :	C₁₁H₁₀ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	USUAZNLPQSKHJH-UHFFFAOYSA-N
M.W :	191.66	Pubchem ID :	234275
Synonyms :

Calculated chemistry of [ 6270-08-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.18
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	56.69
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.58
Log Po/w (XLOGP3) :	3.58
Log Po/w (WLOGP) :	3.51
Log Po/w (MLOGP) :	2.99
Log Po/w (SILICOS-IT) :	4.02
Consensus Log Po/w :	3.33

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.85
Solubility :	0.0269 mg/ml ; 0.00014 mol/l
Class :	Soluble
Log S (Ali) :	-3.54
Solubility :	0.0557 mg/ml ; 0.00029 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.09
Solubility :	0.00154 mg/ml ; 0.00000805 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.44

Safety of [ 6270-08-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6270-08-2 ]

* 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 [ 6270-08-2 ]

[ 6270-08-2 ] Synthesis Path-Downstream 1~102

1
[ 6270-08-2 ]
[ 124-41-4 ]
[ 75896-58-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	In methanol for 17h; Heating;
	at 140℃;

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]
[2]Robson [Biochemical Journal, 1928, vol. 22, p. 1163]

4
[ 6270-08-2 ]
[ 100-63-0 ]
2,6-dimethyl-4-phenylazo-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With paraffin at 200℃; Erhitzen des Reaktionsprodukts mit FeCl₃ in Essigsaeure;

Reference： [1]Backeberg [Journal of the Chemical Society, 1938, p. 1083,1085, 1087]

5
[ 6270-08-2 ]
[ 100-63-0 ]
N-(2,6-dimethyl-[4]quinolyl)-N'-phenyl-hydrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With paraffin oil at 200℃;

Reference： [1]Backeberg [Journal of the Chemical Society, 1938, p. 1083,1085, 1087]

6
[ 6270-08-2 ]
[ 877-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ethanol; water und Zinn;

Reference： [1]Alekseewa [1937, vol. 4, p. 23,26][Chemisches Zentralblatt, 1939, vol. 110, # I, p. 1759]

8
[ 6270-08-2 ]
[ 40807-61-2 ]
[ 87602-53-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine In ethanol for 8h; Heating;

Reference： [1]Sathi; Gujrati; Sharma; Nath; Bhargava; Shanker [Archiv der Pharmazie, 1983, vol. 316, # 9, p. 767 - 772]

9
[ 6270-08-2 ]
[ 6059-17-2 ]
[ 79340-66-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	In ethanol Heating;

Reference： [1]Ahmad; Bhargava; Kishor; Shanker [Pharmazie, 1981, vol. 36, # 6, p. 403 - 404]

10
[ 6270-08-2 ]
[ 1950-68-1 ]
C₁₈H₁₉N₃O₃S [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1982,vol. 59,p. 781 - 782

11
[ 6270-08-2 ]
[ 5188-07-8 ]
[ 123637-61-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	In acetonitrile for 15h; Heating;

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

12
[ 6270-08-2 ]
[ 75291-16-6 ]
[ 87602-52-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridine In ethanol for 8h; Heating;

Reference： [1]Sathi; Gujrati; Sharma; Nath; Bhargava; Shanker [Archiv der Pharmazie, 1983, vol. 316, # 9, p. 767 - 772]

13
[ 6270-08-2 ]
[ 94-09-7 ]
[ 79340-83-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	In ethanol Heating;

Reference： [1]Ahmad; Bhargava; Kishor; Shanker [Pharmazie, 1981, vol. 36, # 6, p. 403 - 404]

14
[ 6270-08-2 ]
[ 123637-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic anhydride; 3-chloro-benzenecarboperoxoic acid Yield given. Multistep reaction;
	With hydrogenchloride; acetic anhydride; 3-chloro-benzenecarboperoxoic acid In chloroform; ethyl acetate; Petroleum ether	2 EXAMPLE 2 To a solution of 4-chloro-2,6-dimethylquinoline (4 g, described in the portion of Example 1 concerned with the preparation of starting materials) in chloroform (50 ml) was added dropwise a solution of m-chloroperbenzoic acid (6.75 g) in chloroform (50 ml). The resulting solution was stirred at laboratory temperature for 18 hours, washed with 10% aqueous sodium carbonate solution (250 ml) and with water (50 ml), and evaporated to dryness. The residue was purified by chromatography on a silica gel column using ethyl acetate as eluent. A mixture of the product so obtained (3 g) and acetic anhydride (30 ml) was stirred at 80° C. for 2 hours, the solvent was evaporated and a mixture of the residue and 10% aqueous hydrochloric acid (25 ml) was stirred at reflux for 30 minutes. The resulting mixture was cooled, basified to pH 14 with aqueous 2N sodium hydroxide solution, and extracted with ethyl acetate (350 ml). The organic extracts were combined and evaporated to drynes. The resulting brown solid was purified by chromatography on a silica gel column using a 3:2 v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) as eluent. There was thus obtained 4-chloro-2-hydroxymethyl-6-methylquinoline (2 g), m.p. 147°-148° C.

15
[ 6270-08-2 ]
[ 123637-33-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane at 77℃; for 3h; Irradiation;
	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane; ethyl acetate; Petroleum ether	1 EXAMPLE 1 A mixture of 4-chloro-2,6-dimethylquinoline (6 g). N-bromosuccinimide (5.96 g), benzoyl peroxide (0.151 g) and carbon tetrachloride (120 ml) was heated at reflux for 3 hours during which time the mixture was illuminated by the light from a 250 Watt light bulb. The resulting mixture was filtered and the filtrate was evaporated to give an orange solid which was purified by chromatography on a silica gel column using a 1:4 v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) as eluent. There was thus obtained 6-bromomethyl-4-chloro-2-methylquinoline (4.7 g), m.p. 111°-113° C.

16
[ 6270-08-2 ]
4-Azido-2,6-dimethyl-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium azide In ethanol; water for 24h; Heating;

Reference： [1]Savini; Massarelli; Pellerano [Il Farmaco, 1993, vol. 48, # 4, p. 515 - 528]

17
[ 15644-82-3 ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate
	With trichlorophosphate at 75℃;
	With trichlorophosphate

With trichlorophosphate for 3h; Reflux;

Reference： [1]Desai, Geeta; Desai, K. K.; Desai, C. M. [Journal of the Indian Chemical Society, 1987, vol. 64, # 6, p. 370 - 371]
[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]Suresh; Nandha Kumar; Mohan [Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 6, p. 778 - 781]
[4]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]

18
[ 25428-07-3 ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In toluene at 90℃; for 3.5h;
65%	With sodium hydroxide; trichlorophosphate In hexane; ethyl acetate	1 EXAMPLE 1 A mixture of 2,6-dimethyl-1H-quinolin-4-one (17.3 g, 100 mmol) and phosphorus oxychloride (30 mL) was heated at 80° C. for 3 h. After cooling down to room temperature, the reaction mixture was poured onto ice. The resulting solution was carefully alkalinized to pH 8-9 with 0.5 N NaOH and saturated Na2CO3. The solution was extracted with CH2Cl2 (200 mL*3). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (10% ethyl acetate in n-hexane) to give 4-chloro-2,6-dimethyl-quinoline (12.4 g, 65% yield).
	With trichlorophosphate at 100℃;

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]
[2]Current Patent Assignee: TAIGEN BIOPHARMACEUTICALS HOLDINGS LTD. - US2004/209902, 2004, A1
[3]Bhupathi, Raja S.; Bandi, Madhu; Ch, Venkata Ramana Reddy; Rama Devi; Dubey [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1236 - 1241]

19
[ 6270-08-2 ]
[ 526-08-9 ]
4-(2,6-Dimethyl-quinolin-4-ylamino)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1996,vol. 35,p. 871 - 873

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride; trichlorophosphate at 130℃;

21
[ 6270-08-2 ]
[ 17356-08-0 ]
S-(2,6-dimethyl-4-quinolyl)thiouronium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetone Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2005, vol. 41, # 5, p. 769 - 771]

22
[ 462-08-8 ]
[ 6270-08-2 ]
[ 870621-00-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	In ethanol for 6.5h; Heating;

Reference： [1]Suresh; Nandha Kumar; Mohan [Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 6, p. 778 - 781]

23
[ 6270-08-2 ]
[ 541-69-5 ]
N-(3-aminophenyl)-2,6-dimethylquinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydrogenchloride In ethanol; water for 8h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1048 - 1051]

24
[ 6270-08-2 ]
[ 16245-77-5 ]
N-(4-aminophenyl)-2,6-dimethylquinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride In ethanol; water for 8h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1048 - 1051]

25
[ 6270-08-2 ]
[ 95-55-6 ]
2-(2,6-dimethylquinolin-4-ylamino)phenol dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride In ethanol; water for 10h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1048 - 1051]

26
[ 6270-08-2 ]
[ 591-27-5 ]
3-(2,6-dimethylquinolin-4-ylamino)phenol dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With hydrogenchloride In ethanol; water for 10h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1048 - 1051]

27
[ 6270-08-2 ]
[ 51-78-5 ]
4-(2,6-dimethylquinolin-4-ylamino)phenol dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydrogenchloride In ethanol; water for 10h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1048 - 1051]

28
[ 6270-08-2 ]
[ 95-54-5 ]
N-(2-aminophenyl)-2,6-dimethylquinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With hydrogenchloride In ethanol; water for 8h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1048 - 1051]

29
[ 6270-08-2 ]
[ 36725-28-7 ]
C₂₂H₂₂N₄O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 382 - 389

30
6-(4-amino-2-hydroxyphenyl)-4,5-dihydropyridazin-3(2H)one [ No CAS ]
[ 6270-08-2 ]
C₂₁H₂₀N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In butan-1-ol for 4h; Heating;

Reference： [1]Abouzid, Khaled; Abdel Hakeem, Maha; Khalil, Omnya; Maklad, Yosria [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 1, p. 382 - 389]

31
[ 6270-08-2 ]
2,6-dimethyl-5,8,12-triaza-benzo[a]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / ethanol / 6.5 h / Heating 2: 65 percent / POCl₃ / 16 h / Heating

Reference： [1]Suresh; Nandha Kumar; Mohan [Chemistry of Heterocyclic Compounds, 2005, vol. 41, # 6, p. 778 - 781]

32
[ 6270-08-2 ]
2,6-dimethyl-4-quinolyl isothiocyanate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / acetone / Heating 2: 39.7 percent / NaOH / H₂O / 1.5 h / Heating

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2005, vol. 41, # 5, p. 769 - 771]

33
[ 6270-08-2 ]
[ 876385-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 95 percent / acetone / Heating 2: 37 percent / NaOH / H₂O / 1.5 h / Heating

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2005, vol. 41, # 5, p. 769 - 771]

34
[ 6270-08-2 ]
2,6-dimethyl-dibenzo[b,h][1,6]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / ethanol / 6 h / Heating 2: 65 percent / POCl₃ / 16 h / Heating

Reference： [1]Suresh; Kumar, R. Nandha; Mohan [Heterocyclic Communications, 2003, vol. 9, # 1, p. 83 - 88]

35
[ 106-49-0 ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) HCl, 2.) acetic anhydride, sulphuric acid 2: phosphorous oxychloride / 75 °C

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]

36
[ 103-89-9 ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: polyphosphoric acid / 5 h / 160 °C 2: phosphorus oxychloride

Reference： [1]Desai, Geeta; Desai, K. K.; Desai, C. M. [Journal of the Indian Chemical Society, 1987, vol. 64, # 6, p. 370 - 371]

37
[ 6270-08-2 ]
[ 123636-66-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 21 percent / 2,6-lutidine / dimethylformamide / 18 h / 70 °C 3: 61 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

38
[ 6270-08-2 ]
[ 123637-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 28 percent / Et₂NSF₃ / CH₂Cl₂ / -70 - 20 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

39
[ 6270-08-2 ]
[ 123637-59-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 59 percent / methanol / 17 h / Heating 2: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

40
[ 6270-08-2 ]
[ 123637-62-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / acetonitrile / 15 h / Heating 2: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

41
[ 6270-08-2 ]
[ 123637-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 28 percent / Et₂NSF₃ / CH₂Cl₂ / -70 - 20 °C 3: 69 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

42
[ 6270-08-2 ]
[ 123637-56-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 48 percent / pyridine / ethyl acetate / 18 h / 60 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

43
[ 6270-08-2 ]
[ 123637-57-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 48 percent / pyridine / ethyl acetate / 18 h / 60 °C 3: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

44
[ 6270-08-2 ]
[ 141848-56-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 3: 87 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

45
[ 6270-08-2 ]
[ 123636-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 3: 94 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

46
[ 6270-08-2 ]
[ 123636-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 3: 92 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

47
[ 6270-08-2 ]
(S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

48
[ 6270-08-2 ]
[ 123637-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 48 percent / pyridine / ethyl acetate / 18 h / 60 °C 3: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 4: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 5: 89 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

49
[ 6270-08-2 ]
[ 123636-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 3: 91 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

50
[ 6270-08-2 ]
[ 123637-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 59 percent / methanol / 17 h / Heating 2: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 3: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 4: 62 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

51
[ 6270-08-2 ]
[ 123637-10-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 98 percent / acetonitrile / 15 h / Heating 2: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 3: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 4: 61 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

52
[ 6270-08-2 ]
(S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

53
[ 6270-08-2 ]
[ 123637-13-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 28 percent / Et₂NSF₃ / CH₂Cl₂ / -70 - 20 °C 3: 69 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 4: 2,6-lutidine / dimethylformamide / 18 h / 70 °C 5: 76 percent / 1 N aq. NaOH / ethanol / 2.5 h / Ambient temperature

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

54
[ 6270-08-2 ]
(S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-ethyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

55
[ 6270-08-2 ]
(S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

56
[ 6270-08-2 ]
(S)-2-{4-[(4-Methoxy-2-methyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 59 percent / methanol / 17 h / Heating 2: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 3: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

57
[ 6270-08-2 ]
(S)-2-{4-[(2-Methyl-4-methylsulfanyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 98 percent / acetonitrile / 15 h / Heating 2: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 3: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

58
[ 6270-08-2 ]
(S)-2-{4-[(4-Chloro-2-fluoromethyl-quinolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 28 percent / Et₂NSF₃ / CH₂Cl₂ / -70 - 20 °C 3: 69 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 4: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

59
[ 6270-08-2 ]
[ 123637-34-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 56 percent / NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 2: 21 percent / 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

60
[ 6270-08-2 ]
(S)-2-{4-[(2-Acetoxymethyl-4-chloro-quinolin-6-ylmethyl)-ethyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) m-chloroperbenzoic acid, 2.) Ac₂O, 3.) 10percent aq. HCl 2: 48 percent / pyridine / ethyl acetate / 18 h / 60 °C 3: NBS, benzoyl peroxide / CCl₄ / 3 h / 77 °C / Irradiation 4: 2,6-lutidine / dimethylformamide / 18 h / 70 °C

Reference： [1]Warner; Barker; Jackman; Burrows; Roberts; Bishop; O'Connor; Hughes [Journal of Medicinal Chemistry, 1992, vol. 35, # 15, p. 2761 - 2768]

61
[ 6270-08-2 ]
[ 93600-19-2 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride In Phosphoroxy chloride	2 2-Trichloromethyl-6-methyl-4-chloroquinoline EXAMPLE 2 2-Trichloromethyl-6-methyl-4-chloroquinoline The mixture of 1.9 g of 2,6-dimethyl-4-chloro-quinoline and 6.5 g of phosphorus pentachloride is heated in 20 ml of phosphoroxy chloride for 3 hours, then the mixture is admixed with ice water and the separated product is filtered. Yield: 2.81 g; 95.1%.

Reference： [1]Current Patent Assignee: SALAMON - US4599345, 1986, A

62
[ 6270-08-2 ]
sodium thiomethoxide [ No CAS ]
[ 123637-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile	2 EXAMPLE 2 A mixture of 4-chloro-2,6-dimethylquinoline (0.5 g, prepared as described in Example 1), sodium thiomethoxide (0.55 g) and dry acetonitrile (20 ml) was heated to reflux under an atmosphere of argon for 15 hours. After cooling to laboratory temperature the mixture was poured into water (50 ml) and extracted with ethyl acetate (2*50 ml). The combined organic layers were dried over magnesium sulphate and evaporated to leave 2,6-dimethyl-4methylthioquinoline as a white solid (0.52 g) which was used without further purification.

Reference： [1]Current Patent Assignee: AKZO NOBEL NV; BOSTON SCIENTIFIC CORP - US5112837, 1992, A

63
[ 124-09-4 ]
[ 6270-08-2 ]
N₁-(2,6-dimethyl-quinolin-4-yl)-hexane-1,5-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydroxide; triethylamine In hexane; pentan-1-ol; ethyl acetate	53 EXAMPLE 53 EXAMPLE 53 Compound 53 was prepared following the procedures described below: 4-Chloro-2,6-dimethyl-quinoline (1.9 g, 10 mmol) obtained in Example 1 and 1,6-hexadiamine (2.3 g, 20 mmol) were dissolved in pentanol (40 mL). The solution was kept under reflux over night. After cooling down to room temperature, 0.5 N NaOH (5 mL) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then extracted with CH2Cl2 (10 mL*3). The organic layer was separated, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (2% Et3N in 1:2 n-hexane and ethyl acetate) to give N1-(2,6-dimethyl-quinolin-4-yl)-hexane-1,5-diamine (1.9 g, 70% yield).

Reference： [1]Current Patent Assignee: TAIGEN BIOPHARMACEUTICALS HOLDINGS LTD. - US2004/209902, 2004, A1

64
[ 6270-08-2 ]
[ 150-13-0 ]
4-(2,6-dimethylquinolin-4-ylamino)benzoic acid dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogenchloride In ethanol; water for 15h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1052 - 1057]

65
[ 6270-08-2 ]
[ 118-92-3 ]
2-(2,6-dimethylquinolin-4-ylamino)benzoic acid dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride In ethanol; water for 15h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1052 - 1057]

66
[ 6270-08-2 ]
[ 94-09-7 ]
ethyl 4-(2,6-dimethylquinolin-4-ylamino)benzoate dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride In ethanol; water for 20h; Heating;

Reference： [1]Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 1052 - 1057]

67
[ 6270-08-2 ]
[ 137-07-5 ]
(4E)-4-[(2-mercaptophenyl)imino]-2,6-dimethyl-1,4-dihydroquinoline dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride In ethanol; water for 5 - 6h; Heating on water bath;

Reference： [1]Location in patent: experimental part Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2008, vol. 44, # 5, p. 723 - 727]

68
[ 6270-08-2 ]
[ 137-07-5 ]
[ 1126485-20-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetone at 20℃; for 48h;

Reference： [1]Location in patent: experimental part Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2008, vol. 44, # 5, p. 723 - 727]

69
[ 6270-08-2 ]
[ 106-47-8 ]
[ 440096-01-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	at 160℃; for 0.5h; neat (no solvent);

Reference： [1]Location in patent: experimental part Manoj, Manickam; Prasad, Karnam Jayaramapillai Rajendra [Journal of Chemical Research, 2009, # 8, p. 485 - 488]

70
[ 6270-08-2 ]
[ 719-59-5 ]
[ 1208362-31-5 ]

Yield	Reaction Conditions	Operation in experiment
23%	at 160℃; for 0.5h; neat (no solvent);

Reference： [1]Location in patent: experimental part Manoj, Manickam; Prasad, Karnam Jayaramapillai Rajendra [Journal of Chemical Research, 2009, # 8, p. 485 - 488]

71
[ 6270-08-2 ]
[ 106-49-0 ]
[ 294667-92-8 ]

Yield	Reaction Conditions	Operation in experiment
50%	at 160℃; for 0.5h; neat (no solvent);
	In neat (no solvent) at 160℃; for 0.5h;

Reference： [1]Location in patent: experimental part Manoj, Manickam; Prasad, Karnam J.R. [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2009, vol. 64, # 7, p. 851 - 857]
[2]Sangeetha; Manoj; Jayabalan; Venkateswaran [Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 845 - 855]

72
[ 6270-08-2 ]
[ 79-19-6 ]
[ 1235445-75-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	In acetone for 30h; Heating;

Reference： [1]Location in patent: experimental part Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2010, vol. 46, # 4, p. 568 - 570]

73
[ 6270-08-2 ]
[ 79-19-6 ]
2-(2,6-dimethylquinolin-4-yl)hydrazinecarbothioamide dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride In ethanol; water Heating;

Reference： [1]Location in patent: experimental part Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2010, vol. 46, # 4, p. 568 - 570]

74
[ 6270-08-2 ]
4-hydrazino-2,6-dimethylquinoline dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; hydrazine In ethanol; water for 15h; Heating;

Reference： [1]Location in patent: experimental part Avetisyan; Aleksanyan; Ambartsumyan [Russian Journal of Organic Chemistry, 2010, vol. 46, # 3, p. 427 - 431]

75
[ 6270-08-2 ]
[ 1372538-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0.5 h / 160 °C / neat (no solvent) 2: phosphorus pentoxide; phosphoric acid / 5 h / 160 °C

Reference： [1]Manoj; Prasad, K.J. Rajendra [Synthetic Communications, 2012, vol. 42, # 3, p. 434 - 446]

76
[ 6270-08-2 ]
[ 1372538-11-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 0.5 h / 160 °C / neat (no solvent) 2: phosphorus pentoxide; phosphoric acid / 5 h / 160 °C

Reference： [1]Manoj; Prasad, K.J. Rajendra [Synthetic Communications, 2012, vol. 42, # 3, p. 434 - 446]

77
[ 6270-08-2 ]
[ 551-93-9 ]
[ 1372538-07-2 ]

Yield	Reaction Conditions	Operation in experiment
30%	at 160℃; for 0.5h; neat (no solvent);

Reference： [1]Location in patent: experimental part Manoj; Prasad, K.J. Rajendra [Synthetic Communications, 2012, vol. 42, # 3, p. 434 - 446]

78
[ 6270-08-2 ]
[ 2835-77-0 ]
[ 1372538-11-8 ]

Yield	Reaction Conditions	Operation in experiment
23%	at 160℃; for 0.5h; neat (no solvent);

Reference： [1]Location in patent: experimental part Manoj; Prasad, K.J. Rajendra [Synthetic Communications, 2012, vol. 42, # 3, p. 434 - 446]

79
[ 6270-08-2 ]
[ 1373399-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 0.5 h / 190 °C / Neat (no solvent) 2.1: polyphosphoric acid / 3 h / 160 °C 2.2: Cooling with ice

Reference： [1]Prabha; Prasad, K. J. Rajendra [Synthetic Communications, 2012, vol. 42, # 15, p. 2277 - 2289]

80
[ 6270-08-2 ]
[ 134-32-7 ]
[ 332165-34-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	at 190℃; for 0.5h; Neat (no solvent);

Reference： [1]Location in patent: experimental part Prabha; Prasad, K. J. Rajendra [Synthetic Communications, 2012, vol. 42, # 15, p. 2277 - 2289]

81
[ 106-49-0 ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: ethanol / 4 h / Reflux 2: diphenylether / 1 h / 250 °C 3: trichlorophosphate / 100 °C
	Multi-step reaction with 3 steps 1: methanol / 7 h / 40 °C 2: diphenylether / 0.5 h / Reflux 3: trichlorophosphate / 3 h / Reflux

Reference： [1]Bhupathi, Raja S.; Bandi, Madhu; Ch, Venkata Ramana Reddy; Rama Devi; Dubey [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1236 - 1241]
[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]

82
ethyl 3-(p-tolylamino)but-2-enoate [ No CAS ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diphenylether / 0.5 h / Reflux 2: trichlorophosphate / 3 h / 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]

83
[ 6270-08-2 ]
[ 29125-48-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 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]

84
[ 6270-08-2 ]
[ 1350539-16-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrazine hydrate / Reflux 2: 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]

85
[ 6270-08-2 ]
2,6,9-trimethyldibenzo[b,h][1,6]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: neat (no solvent) / 0.5 h / 160 °C 2.1: trichlorophosphate / 0.5 h / 0 °C 2.2: 10 h / 100 °C
	Multi-step reaction with 2 steps 1: neat (no solvent) / 0.5 h / 160 °C 2: phosphorus pentoxide; phosphoric acid / 5 h / 200 °C

Reference： [1]Sangeetha; Manoj; Jayabalan; Venkateswaran [Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 845 - 855]
[2]Sangeetha; Manoj; Jayabalan; Venkateswaran [Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 845 - 855]

86
[ 6270-08-2 ]
2,6,9-trimethyldibenzo[b,h][1,6]naphthyridine [ No CAS ]
2,6,9-trimethyl-7-(3',4'-dihydroxyphenyl)dibenzo[b,h][1,6]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: neat (no solvent) / 0.5 h / 160 °C 2: phosphorus pentoxide; phosphoric acid / 5 h / 160 °C

Reference： [1]Sangeetha; Manoj; Jayabalan; Venkateswaran [Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 845 - 855]

87
[ 6270-08-2 ]
2,6,9-trimethyldibenzo[b,h][1,6]naphthyridine [ No CAS ]
2,6,9-trimethyl-7-(2'-hydroxyphenyl)dibenzo[b,h][1,6]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: neat (no solvent) / 0.5 h / 160 °C 2: phosphorus pentoxide; phosphoric acid / 5 h / 160 °C

Reference： [1]Sangeetha; Manoj; Jayabalan; Venkateswaran [Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 845 - 855]

88
[ 6270-08-2 ]
[ 134469-07-1 ]
4-((1H-benzo[d]imidazol-2-yl)thio)-2,6-dimethylquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polyethylene glycol-600 at 100℃; for 0.5h; Green chemistry;

Reference： [1]Bhupathi, Raja S.; Bandi, Madhu; Ch, Venkata Ramana Reddy; Rama Devi; Dubey [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1236 - 1241]

89
[ 6270-08-2 ]
[ 42956-80-9 ]
2-((2,6-dimethylquinolin-4-yl)thio)-6-methylpyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polyethylene glycol-600 at 100℃; for 0.5h; Green chemistry;

Reference： [1]Bhupathi, Raja S.; Bandi, Madhu; Ch, Venkata Ramana Reddy; Rama Devi; Dubey [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1236 - 1241]

90
[ 6270-08-2 ]
[ 13906-09-7 ]
2-((2,6-dimethylquinolin-4-yl)thio)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With polyethylene glycol-600 at 100℃; for 0.5h; Green chemistry;

Reference： [1]Bhupathi, Raja S.; Bandi, Madhu; Ch, Venkata Ramana Reddy; Rama Devi; Dubey [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1236 - 1241]

91
ethyl β-(4-tolylimino)-butyrate [ No CAS ]
[ 6270-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: diphenylether / 1 h / 250 °C 2: trichlorophosphate / 100 °C

Reference： [1]Bhupathi, Raja S.; Bandi, Madhu; Ch, Venkata Ramana Reddy; Rama Devi; Dubey [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 2, p. 1236 - 1241]

92
[ 6270-08-2 ]
2-[(2,6-dimethylquinolin-4-yl)sulfanyl]acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetone / 72 h / 20 °C 2: hydrazine hydrate / ethanol / 20 °C

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

93
[ 6270-08-2 ]
2-[(2,6-dimethylquinolin-4-yl)sulfanyl]acetyl}-N-phenylhydrazine-1-carbothioamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: acetone / 72 h / 20 °C 2: hydrazine hydrate / ethanol / 20 °C 3: ethanol / Heating

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

94
[ 6270-08-2 ]
5-[(2,6-dimethylquinolin-4-yl)sulfanyl]methyl}-4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetone / 72 h / 20 °C 2: hydrazine hydrate / ethanol / 20 °C 3: ethanol / Heating 4: sodium hydroxide / 3 h / Heating

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

95
[ 6270-08-2 ]
5-[(2,6-dimethylquinolin-4-yl)sulfanyl]methyl}-N-phenyl-1,3,4-thiadiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetone / 72 h / 20 °C 2: hydrazine hydrate / ethanol / 20 °C 3: ethanol / Heating 4: sulfuric acid / 3 h / 20 °C

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

96
[ 6270-08-2 ]
2-[(2,6-dimethylquinolin-4-yl)sulfanyl]-N'-(4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene)acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetone / 72 h / 20 °C 2: hydrazine hydrate / ethanol / 20 °C 3: ethanol / Heating 4: sodium acetate / ethanol / Heating

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

97
[ 6270-08-2 ]
N'-[3,4-diphenyl-1,3-thiazol-2(3H)-ylidene]-2-[(2,6-dimethylquinolin-4-yl)sulfanyl]acetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetone / 72 h / 20 °C 2: hydrazine hydrate / ethanol / 20 °C 3: ethanol / Heating 4: sodium acetate / ethanol / Heating

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

98
[ 6270-08-2 ]
[ 2365-48-2 ]
methyl [(2,6-dimethylquinolin-4-yl)sulfanyl]acetate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In acetone at 20℃; for 72h;	Compounds 2a-2c. General procedure: A mixture of 0.01 mol of compound 1a-1c [17], 10 mL of anhydrous acetone, and 0.9 mL (0.01 mol) of methyl sulfanylacetate was stirred for 3 days at room temperature. The obtained precipitate was filtered off and washed with anhydrous acetone.

Reference： [1]Aleksanyan; Hambardzumyan [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 226 - 230][Zh. Org. Khim., 2017, vol. 53, # 2, p. 233 - 236]

99
[ 6270-08-2 ]
(4-chloro-3-formylphenyl)boronic acid [ No CAS ]
[ 95-54-5 ]
3-(2,6-dimethylquinolin-4-yl)benzo[d]benzo[3,4]azeto[1,2-a]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 4-chloro-2,6-dimethylquinoline; (4-chloro-3-formylphenyl)boronic acid Stage #2: 1,2-diamino-benzene In toluene at 30℃; Stage #3: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos In toluene at 100℃; for 11h;	General procedure for the synthesis of 3a General procedure: An oven-dried schlenk tube was charged with a magnetic stir bar, 2-Chloro-5-(2-methyl) quinoline-4-yl) benzaldehyde 1a (10 mmol), o-phenylenediamine 2 (10 mmol) and Toluene (50 mL). The tube was placed in a preheated oil bath at 30 °C temperature and the reaction slurry was stirred vigorously for 3-6 h with continuous air bubbling. The air bubbling was stopped after completion of the reaction (TLC, 20 % Ethyl acetate in Hexane) and Cs2CO3 (1.4 mmol), Xphos (5 mol%) and Pd2(dba)3 (3 mol%) were added. The reaction mixture was further heated at 100 °C and stirred for 9-13 h. Finally the reaction mixture was cooled to room temperature and filtered through a pad of Celite eluting with ethyl acetate. The filtrate was concentrated and purification was done by silica gel column chromatography (20 % Ethyl acetate in Hexane) gave the desired product 3a.

Reference： [1]Patel, Janki J.; Patel, Anuj P.; Chikhalia, Kishor H. [Synthetic Communications, 2021, vol. 51, # 1, p. 81 - 93]

100
[ 6270-08-2 ]
[ 132-32-1 ]
3-(N-(2,6-dimethylquinolin-4-yl)amino)-9-ethyl-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With copper (I) iodide; potassium carbonate In N,N-dimethyl-formamide at 120℃;

Reference： [1]Ezhumalai, Yamuna; Karnam Jayarampillai, Rajendra Prasad; Kumaresan, Prabakaran; Matthias, Zeller [Journal of Heterocyclic Chemistry, 2022]

101
[ 6270-08-2 ]
C₄₁H₃₃N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper (I) iodide; potassium carbonate / N,N-dimethyl-formamide / 120 °C 2: polyphosphoric acid / 160 °C

Reference： [1]Ezhumalai, Yamuna; Karnam Jayarampillai, Rajendra Prasad; Kumaresan, Prabakaran; Matthias, Zeller [Journal of Heterocyclic Chemistry, 2022]

102
[ 6270-08-2 ]
12-benzoyl-9-ethyl-2,6-dimethyl-7-phenyl-9H-benzo[h]carbazol[3,2-b][1,6]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper (I) iodide; potassium carbonate / N,N-dimethyl-formamide / 120 °C 2: polyphosphoric acid / 160 °C

Reference： [1]Ezhumalai, Yamuna; Karnam Jayarampillai, Rajendra Prasad; Kumaresan, Prabakaran; Matthias, Zeller [Journal of Heterocyclic Chemistry, 2022]

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Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Chloroalkane Synthesis with SOCI2 • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Historical Records

Related Functional Groups of
[ 6270-08-2 ]

Chlorides

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Quinolines

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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 6270-08-2 ] {[proInfo.proName]}

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[ 6270-08-2 ] Synthesis Path-Downstream 1~102

Technical Information

Related Functional Groups of [ 6270-08-2 ]

Chlorides

Related Parent Nucleus of [ 6270-08-2 ]

Quinolines

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[ 6270-08-2 ]

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[ 6270-08-2 ]