Home Cart 0 Sign in  
X

[ CAS No. 6270-08-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 6270-08-2
Chemical Structure| 6270-08-2
Chemical Structure| 6270-08-2
Structure of 6270-08-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Quality Control of [ 6270-08-2 ]

Related Doc. of [ 6270-08-2 ]

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 ]

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 Ų

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   1~69

  • 1
  • [ 6270-08-2 ]
  • [ 124-41-4 ]
  • [ 75896-58-1 ]
YieldReaction ConditionsOperation in experiment
59% In methanol for 17h; Heating;
at 140℃;
  • 4
  • [ 6270-08-2 ]
  • [ 100-63-0 ]
  • 2,6-dimethyl-4-phenylazo-quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With paraffin at 200℃; Erhitzen des Reaktionsprodukts mit FeCl3 in Essigsaeure;
  • 5
  • [ 6270-08-2 ]
  • [ 100-63-0 ]
  • <i>N</i>-(2,6-dimethyl-[4]quinolyl)-<i>N</i>'-phenyl-hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With paraffin oil at 200℃;
  • 6
  • [ 6270-08-2 ]
  • [ 877-43-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ethanol; water und Zinn;
  • 8
  • [ 6270-08-2 ]
  • [ 40807-61-2 ]
  • [ 87602-53-7 ]
YieldReaction ConditionsOperation in experiment
80% With pyridine In ethanol for 8h; Heating;
  • 9
  • [ 6270-08-2 ]
  • [ 6059-17-2 ]
  • [ 79340-66-2 ]
YieldReaction ConditionsOperation in experiment
70% In ethanol Heating;
  • 10
  • [ 6270-08-2 ]
  • [ 1950-68-1 ]
  • C18H19N3O3S [ No CAS ]
  • 11
  • [ 6270-08-2 ]
  • [ 5188-07-8 ]
  • [ 123637-61-6 ]
YieldReaction ConditionsOperation in experiment
98% In acetonitrile for 15h; Heating;
  • 12
  • [ 6270-08-2 ]
  • [ 75291-16-6 ]
  • [ 87602-52-6 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine In ethanol for 8h; Heating;
  • 13
  • [ 6270-08-2 ]
  • [ 94-09-7 ]
  • [ 79340-83-3 ]
YieldReaction ConditionsOperation in experiment
55% In ethanol Heating;
  • 14
  • [ 6270-08-2 ]
  • [ 123637-58-1 ]
YieldReaction ConditionsOperation 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 (2*50 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 (3*50 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 ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation in experiment
With sodium azide In ethanol; water for 24h; Heating;
  • 18
  • [ 25428-07-3 ]
  • [ 6270-08-2 ]
YieldReaction ConditionsOperation 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℃;
  • 19
  • [ 6270-08-2 ]
  • [ 526-08-9 ]
  • 4-(2,6-Dimethyl-quinolin-4-ylamino)-N-(2-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation 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 ]
YieldReaction ConditionsOperation in experiment
95% In acetone Heating;
  • 22
  • [ 462-08-8 ]
  • [ 6270-08-2 ]
  • [ 870621-00-4 ]
YieldReaction ConditionsOperation in experiment
82% In ethanol for 6.5h; Heating;
  • 23
  • [ 6270-08-2 ]
  • [ 541-69-5 ]
  • N-(3-aminophenyl)-2,6-dimethylquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride In ethanol; water for 8h; Heating;
  • 24
  • [ 6270-08-2 ]
  • [ 16245-77-5 ]
  • N-(4-aminophenyl)-2,6-dimethylquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In ethanol; water for 8h; Heating;
  • 25
  • [ 6270-08-2 ]
  • [ 95-55-6 ]
  • 2-(2,6-dimethylquinolin-4-ylamino)phenol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride In ethanol; water for 10h; Heating;
  • 26
  • [ 6270-08-2 ]
  • [ 591-27-5 ]
  • 3-(2,6-dimethylquinolin-4-ylamino)phenol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride In ethanol; water for 10h; Heating;
  • 27
  • [ 6270-08-2 ]
  • [ 51-78-5 ]
  • 4-(2,6-dimethylquinolin-4-ylamino)phenol dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With hydrogenchloride In ethanol; water for 10h; Heating;
  • 28
  • [ 6270-08-2 ]
  • [ 95-54-5 ]
  • N-(2-aminophenyl)-2,6-dimethylquinolin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With hydrogenchloride In ethanol; water for 8h; Heating;
  • 29
  • [ 6270-08-2 ]
  • [ 36725-28-7 ]
  • C22H22N4O [ No CAS ]
  • 30
  • 6-(4-amino-2-hydroxyphenyl)-4,5-dihydropyridazin-3(2H)one [ No CAS ]
  • [ 6270-08-2 ]
  • C21H20N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In butan-1-ol for 4h; Heating;
  • 31
  • [ 6270-08-2 ]
  • 2,6-dimethyl-5,8,12-triaza-benzo[<i>a</i>]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / ethanol / 6.5 h / Heating 2: 65 percent / POCl3 / 16 h / Heating
  • 32
  • [ 6270-08-2 ]
  • 2,6-dimethyl-4-quinolyl isothiocyanate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / acetone / Heating 2: 39.7 percent / NaOH / H2O / 1.5 h / Heating
  • 33
  • [ 6270-08-2 ]
  • [ 876385-41-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / acetone / Heating 2: 37 percent / NaOH / H2O / 1.5 h / Heating
  • 34
  • [ 6270-08-2 ]
  • 2,6-dimethyl-dibenzo[<i>b</i>,<i>h</i>][1,6]naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / ethanol / 6 h / Heating 2: 65 percent / POCl3 / 16 h / Heating
  • 35
  • [ 106-49-0 ]
  • [ 6270-08-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) HCl, 2.) acetic anhydride, sulphuric acid 2: phosphorous oxychloride / 75 °C
  • 36
  • [ 103-89-9 ]
  • [ 6270-08-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: polyphosphoric acid / 5 h / 160 °C 2: phosphorus oxychloride
  • 37
  • [ 6270-08-2 ]
  • [ 123636-66-8 ]
YieldReaction ConditionsOperation 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
  • 38
  • [ 6270-08-2 ]
  • [ 123637-70-7 ]
YieldReaction ConditionsOperation 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
  • 39
  • [ 6270-08-2 ]
  • [ 123637-59-2 ]
YieldReaction ConditionsOperation 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
  • 40
  • [ 6270-08-2 ]
  • [ 123637-62-7 ]
YieldReaction ConditionsOperation 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
  • 41
  • [ 6270-08-2 ]
  • [ 123637-71-8 ]
YieldReaction ConditionsOperation 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
  • 42
  • [ 6270-08-2 ]
  • [ 123637-56-9 ]
YieldReaction ConditionsOperation 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
  • 43
  • [ 6270-08-2 ]
  • [ 123637-57-0 ]
YieldReaction ConditionsOperation 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
  • 44
  • [ 6270-08-2 ]
  • [ 141848-56-8 ]
YieldReaction ConditionsOperation 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
  • 45
  • [ 6270-08-2 ]
  • [ 123636-91-9 ]
YieldReaction ConditionsOperation 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
  • 46
  • [ 6270-08-2 ]
  • [ 123636-90-8 ]
YieldReaction ConditionsOperation 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
  • 47
  • [ 6270-08-2 ]
  • (S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 48
  • [ 6270-08-2 ]
  • [ 123637-06-9 ]
YieldReaction ConditionsOperation 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
  • 49
  • [ 6270-08-2 ]
  • [ 123636-89-5 ]
YieldReaction ConditionsOperation 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
  • 50
  • [ 6270-08-2 ]
  • [ 123637-07-0 ]
YieldReaction ConditionsOperation 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
  • 51
  • [ 6270-08-2 ]
  • [ 123637-10-5 ]
YieldReaction ConditionsOperation 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
  • 52
  • [ 6270-08-2 ]
  • (S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-methyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 53
  • [ 6270-08-2 ]
  • [ 123637-13-8 ]
YieldReaction ConditionsOperation 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
  • 54
  • [ 6270-08-2 ]
  • (S)-2-{4-[(4-Chloro-2-methyl-quinolin-6-ylmethyl)-ethyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 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 ]
YieldReaction ConditionsOperation 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
  • 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 ]
YieldReaction ConditionsOperation 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
  • 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 ]
YieldReaction ConditionsOperation 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
  • 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 ]
YieldReaction ConditionsOperation 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
  • 59
  • [ 6270-08-2 ]
  • [ 123637-34-3 ]
YieldReaction ConditionsOperation 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
  • 60
  • [ 6270-08-2 ]
  • (S)-2-{4-[(2-Acetoxymethyl-4-chloro-quinolin-6-ylmethyl)-ethyl-amino]-benzoylamino}-pentanedioic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 61
  • [ 6270-08-2 ]
  • [ 93600-19-2 ]
YieldReaction ConditionsOperation 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%.
  • 62
  • [ 6270-08-2 ]
  • sodium thiomethoxide [ No CAS ]
  • [ 123637-61-6 ]
YieldReaction ConditionsOperation 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.
  • 63
  • [ 124-09-4 ]
  • [ 6270-08-2 ]
  • N1-(2,6-dimethyl-quinolin-4-yl)-hexane-1,5-diamine [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 64
  • [ 6270-08-2 ]
  • [ 150-13-0 ]
  • 4-(2,6-dimethylquinolin-4-ylamino)benzoic acid dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride In ethanol; water for 15h; Heating;
  • 65
  • [ 6270-08-2 ]
  • [ 118-92-3 ]
  • 2-(2,6-dimethylquinolin-4-ylamino)benzoic acid dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In ethanol; water for 15h; Heating;
  • 66
  • [ 6270-08-2 ]
  • [ 94-09-7 ]
  • ethyl 4-(2,6-dimethylquinolin-4-ylamino)benzoate dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride In ethanol; water for 20h; Heating;
  • 67
  • [ 6270-08-2 ]
  • [ 137-07-5 ]
  • (4E)-4-[(2-mercaptophenyl)imino]-2,6-dimethyl-1,4-dihydroquinoline dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In ethanol; water for 5 - 6h; Heating on water bath;
  • 68
  • [ 6270-08-2 ]
  • [ 137-07-5 ]
  • [ 1126485-20-8 ]
YieldReaction ConditionsOperation in experiment
80% In acetone at 20℃; for 48h;
  • 69
  • [ 6270-08-2 ]
  • [ 106-47-8 ]
  • [ 440096-01-5 ]
YieldReaction ConditionsOperation in experiment
70% at 160℃; for 0.5h; neat (no solvent);
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 6270-08-2 ]

Chlorides

Chemical Structure| 74949-20-5

[ 74949-20-5 ]

4-Chloro-2,7-dimethylquinoline

Similarity: 0.98

Chemical Structure| 1378260-82-2

[ 1378260-82-2 ]

5-Chloro-2,7-dimethylquinoline

Similarity: 0.98

Chemical Structure| 63136-64-1

[ 63136-64-1 ]

4-Chloro-2,5,7-trimethylquinoline

Similarity: 0.95

Chemical Structure| 63136-63-0

[ 63136-63-0 ]

4-Chloro-2,5-dimethylquinoline

Similarity: 0.95

Chemical Structure| 53342-53-3

[ 53342-53-3 ]

4,6-Dichloro-2-methylquinoline

Similarity: 0.95

Related Parent Nucleus of
[ 6270-08-2 ]

Quinolines

Chemical Structure| 74949-20-5

[ 74949-20-5 ]

4-Chloro-2,7-dimethylquinoline

Similarity: 0.98

Chemical Structure| 1378260-82-2

[ 1378260-82-2 ]

5-Chloro-2,7-dimethylquinoline

Similarity: 0.98

Chemical Structure| 63136-64-1

[ 63136-64-1 ]

4-Chloro-2,5,7-trimethylquinoline

Similarity: 0.95

Chemical Structure| 63136-63-0

[ 63136-63-0 ]

4-Chloro-2,5-dimethylquinoline

Similarity: 0.95

Chemical Structure| 53342-53-3

[ 53342-53-3 ]

4,6-Dichloro-2-methylquinoline

Similarity: 0.95