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[ CAS No. 22190-40-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 22190-40-5
Chemical Structure| 22190-40-5
Chemical Structure| 22190-40-5
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Product Details of [ 22190-40-5 ]

CAS No. :22190-40-5 MDL No. :MFCD05664819
Formula : C11H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :BHQKJGRWIRTURN-UHFFFAOYSA-N
M.W : 254.12 Pubchem ID :89622
Synonyms :

Calculated chemistry of [ 22190-40-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.95
TPSA : 20.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.37
Log Po/w (MLOGP) : 2.73
Log Po/w (SILICOS-IT) : 2.81
Consensus Log Po/w : 2.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.15
Solubility : 0.178 mg/ml ; 0.000702 mol/l
Class : Soluble
Log S (Ali) : -2.43
Solubility : 0.951 mg/ml ; 0.00374 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.76
Solubility : 0.0446 mg/ml ; 0.000175 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.84

Safety of [ 22190-40-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 22190-40-5 ]

* 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 [ 22190-40-5 ]

[ 22190-40-5 ] Synthesis Path-Downstream   1~21

YieldReaction ConditionsOperation in experiment
With bromine; acetic acid
  • 2
  • [ 4169-19-1 ]
  • [ 22190-40-5 ]
YieldReaction ConditionsOperation in experiment
96% With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 20℃; for 3h; Crude 1- (3, 4-dihydro-2H-quinolin-1-yl)-ethanone was dissolved in DMF (60 mL), and N-bromo succinimide (100 mmol) was added portion wise. Stirred at room temperature for 3h, then the reaction mixture was poured into water (150 mL) and extracted with ethyl acetate. The organic phase was washed with NH4C1 (sat. ), dried over MgS04, filtered and evaporated. Yield: 96% 1H NMR (D6-DMSO) : 1.85 (m, 2H); 2.16 (s, 3H); 2.70 (m, 2H); 3.66 (m, 2H); 7.25- 7.60 (3H).
90% With N-Bromosuccinimide In dichloromethane at 0 - 45℃; for 16h;
90% With N-Bromosuccinimide In dichloromethane at 0 - 45℃; for 16h; 87.2 Step 2 To a solution of 1-(3,4-dihydro-2H-quinolin-1-yl)ethanone (400 mg,2.0 mmol)in DCM(10 mL)at 0 °C was added N-bromosuccinimide (400 mg,2.0 mmol)portionwise. The mixturewas stirred at room temperature for 2 h,then heated at 45 °C for 14 h. After cooling to roomtemperature,the reaction was concentrated under reduced pressure. The residue was purified by silica gel chromatography (100% Heptanes to 60% EtOAc in Heptanes gradient)to afford thetitle compound (0.542 g,90%)as a yellow oil. 1HNMR (400 MHz,CDCl3)8 7.40-7.03 (m,3H),3.76 (t,J = 6.5 Hz,2H),2.71 (t,J = 6.6 Hz,2H),2.22 (s,3H),2.04- 1.86 (m,2H).
  • 3
  • [ 22190-40-5 ]
  • [ 851202-94-3 ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 1-(6-bromo-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one With copper(I) cyanide In DMF (N,N-dimethyl-formamide) for 18h; Heating / reflux; Stage #2: With ammonia In DMF (N,N-dimethyl-formamide); water 1-(6-Bromo-3, 4-dihydro-2H-quinolin-l-yl)-ethanone (96 mmol) was dissolved in DMF (60 mL) and CuCN (200 mmol) was added. The reaction mixture was refluxed for 18h, then cooled and poured into water (400 mL). Aq. NH3 (sat. ) (100 mL) was added, and the mixture was stirred vigorously until it had turned blue. The product had precipitated and was removed by filtration, washed with water and dried. Yield: 53% 1H NMR (D6-DMSO) : 1.78 (m, 2H); 2.67 (m, 2H); 3.23 (m, 2H); 6.43 (d, 1H); 7.41- 7.47 (2H). m/z: 201 (MH+)
YieldReaction ConditionsOperation in experiment
17 Methoxylation of 6-Bromo-1-Acetyl-1,2,3,4-Tetrahydroquinoline with subsequent hydrolysis to yield 6-Methoxy-1,2,3,4-Tetrahydroquinoline Hydrochloride The crude product was dissolved in isopropanol (210 ml) and treated with 16% w/w hydrogen chloride in isopropanol (125 ml). On cooling the hydrochloride salt crystallized out. Filtration and drying gave pure 6-methoxy-1,2,3,4-tetrahydroquinoline hydrochloride, m.p. 150° to 152° C. (yield 66 g: 75% of theory).
  • 5
  • [ 5263-87-6 ]
  • [ 22190-40-5 ]
YieldReaction ConditionsOperation in experiment
67% 8 Methoxylation of 6-Bromo-1-Acetyl-1,2,3,4-Tetrahydroquinoline with subsequent hydrolysis to yield 6-Methoxy-1,2,3,4-Tetrahydroquinoline Its infra-red spectrum was identical to that of authentic material obtained by the hydrogenation of 6-methoxyquinoline. Overall yield=67%.
YieldReaction ConditionsOperation in experiment
Stage #1: In 1,2-dichloro-ethane at 20℃; Inert atmosphere; Stage #2: With N-Bromosuccinimide In N,N-dimethyl-formamide 28.1 Step 1
1-(6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one General procedure: Step 11-(6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneTo a solution of the 2-methyl-1,2,3,4-tetrahydroquinoline (5g, 36.96 mmol) in 1,2-dichloroethane (34 mL) was added acetic anhydride (4.26 mL, 50 mmol) and the reaction stirred at ambient temperature for 4 hours under nitrogen atmosphere. A further 1 mL of acetic anhydride was added and the reaction mixture stirred overnight. The solvents were removed in vacuo to afford a liquid which was dissolved in EtOAc (60 mL) and the organic phase was then washed sequentially with water (50 mL), 1 N NaOH (aq) (50 mL), water (50 mL) and sat NaCI (aq) (50 mL), then dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo to afford a yellow oil. The product was dissolved in DMF (26 mL) and N-bromosuccinimide (6.20 g, 34.86 mmol) was added in portions and mixture then stirred overnight. The reaction mixture was partitioned between EtOAc (200 mL) and water (100 mL). The organic phase was separated then washed with saturated aqueous ammonium chloride solution (100 mL) then sat. NaCI (aq) (2 x 50 mL). The reaction mixture was dried over magnesium sulphate, filtered and filtrate evaporated in vacuo to afford product as a yellow oil (9.3 g, quant.).LC/MS (method B): RT = 1.28 min; m/z = 268 [M+H]+. Total run time 1.90 mins.
  • 7
  • [ 22190-40-5 ]
  • 6-bromo-2-methyl- 1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With hydrogenchloride In water for 5h; Reflux; 83.1 Step 1
6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline Step 16-bromo-2-methyl-1,2,3,4-tetrahydroquinolineTo a suspension of 1-(6-bromo-2-methyl-1 ,2,3,4-tetrahydroquinolin-1-yl)ethan-1- one (example 15, step 1) (5.16 g, 19.24 mmol) in water (15 mL) was added cone HCI (12N, 25 mL) and the mixture was heated to reflux for 5 hours then allowed to cool to ambient temperature. Further water was added and the pH of the mixture adjusted to pH = 4 by cautious addition of solid NaOH pellets. The precipitate was filtered off and washed with water then iso-hexane and dried in vacuo to afford 6-bromo-2-methyl-1 ,2,3,4-tetrahydroquinoline as an off-white solid (2.07 g, 48%).LC/MS (method B): RT = 1.41 min; m/z = 226 [M+H]+. Total run time 1.90 mins.
  • 8
  • [ 22190-40-5 ]
  • 3-(acetyloxy)-4-(6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline-1-carbonyl)phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / water / 5 h / Reflux 2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2.2: 1.5 h / 20 °C
  • 9
  • [ 22190-40-5 ]
  • 3-(acetyloxy)-4-[2-methyl-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water / 5 h / Reflux 2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2.2: 1.5 h / 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere
  • 10
  • [ 22190-40-5 ]
  • 4-[2-methyl-6-(3-methylpyridin-2-yl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]benzene-1,3-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogenchloride / water / 5 h / Reflux 2.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide 2.2: 1.5 h / 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 4.1: 1,1'-bis-(diphenylphosphino)ferrocene; potassium carbonate / water; acetonitrile / 1 h / 80 °C / Inert atmosphere
  • 11
  • [ 22190-40-5 ]
  • 1-methyl-7-(difluoromethyl)-6-(1-methylpyrazol-4-yl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
  • 1-[6-[7-(difluoromethyl)-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-3,4-dihydro-2H-quinolin-1-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II); sodium t-butanolate In 1,4-dioxane at 120℃; for 16h; Inert atmosphere;
  • 12
  • [ 635-46-1 ]
  • [ 22190-40-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 0 - 32 °C 2: N-Bromosuccinimide / dichloromethane / 16 h / 0 - 45 °C
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2.5 h / 0 - 32 °C 2: N-Bromosuccinimide / dichloromethane / 16 h / 0 - 45 °C
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 0 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C
  • 13
  • [ 22190-40-5 ]
  • [ 611-73-4 ]
  • C18H16BrNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate In 1,2-dichloro-ethane at 20℃; for 10h; Irradiation;
  • 14
  • [ 22190-40-5 ]
  • 1-[6-(1,3,6,2-dioxazaborocan-2-yl)-3,4-dihydro-2H-quinolin-1-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 1 h / 110 °C / Microwave irradiation 2: dichloromethane / 36 h
  • 15
  • [ 22190-40-5 ]
  • (1-acetyl-3,4-dihydro-2H-quinolin-6-yl)boronic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 1 h / 110 °C / Microwave irradiation 2: dichloromethane / 36 h 3: hydrogenchloride / water / 2 h
  • 16
  • [ 22190-40-5 ]
  • [ 73183-34-3 ]
  • 1-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-quinolin-1-yl]ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.4 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 110℃; for 1h; Microwave irradiation; Synthesis of (l-acetyl-3,4-dihydro-2H-quinolin-6-yl)boronic acid (N-001). A mixture of 1.5 g (5.9 mmol) of l-(6-bromo-3,4-dihydro-2H-quinolin-l-yl)ethanone, 2.3 g (8.9 mmol) of bis(pinacolato)diboron, 1.7 g (19 mmol) of KOAc and 0.49 g (0.59 mmol) of Pd(dppf)- CH2CI2 in 8 ml of degasses 1,4-dioxane is heated to 110 °C with microwave irradiation for 1 h. The mixture is filtered, concentrated, and purified by flash chromatography (0-7% MeOH in CH2CI2) to provide 1.4 g (4.5 mmol) of l-[6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydro-2H-quinolin- l-yl]ethanone (I-AAW). (0185) A mixture of 1.4 g (4.5 mmol) of I-AAW, 2.4 g (23 mmol) of diethanolamine, and 10 mL of CH2CI2 is stirred for 36 h. The mixture is concentrated and purified by flash chromatography (0- 10% MeOH in CH2C12) to provide 0.46 g (1.5 mmol) of l-[6-(l,3,6,2-dioxazaborocan-2-yl)-3,4- dihydro-2H-quinolin- l-yl]ethanone (I-AAX). (0186) I-AAX (0.22 g, 0.75 mmol) is stirred with 1 mL of 1M HCl for 2h. A solid is generated, that is filtered and dried to provide 0.10 g (0.46 mmol) of N-001.
  • 17
  • [ 22190-35-8 ]
  • [ 75-36-5 ]
  • [ 22190-40-5 ]
YieldReaction ConditionsOperation in experiment
90% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 4h; To a solution of <strong>[22190-35-8]6-bromo-1,2,3,4-tetrahydroquinoline</strong> (13.1 g, 14.6 mmol) and DIPEA (6.5 mL, 36.5 mmol) in DCM (30 mL) at 0, was added AcCl (1.72 g, 21.9 mmol) in one portion. The reaction mixture was stirred at RT for 4 h, then quenched with water. It was extracted with EA, the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give 1-(6-bromo-3,4-dihydroquinolin -1(2H)-yl)ethan-1-one as a light- yellow oil (3.33 g, 90%). LC-MS (ESI): m/z (M+H)+ = 254.06/256.06
  • 18
  • [ 22190-40-5 ]
  • 4-(1-acetyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 10 h / 100 °C 2: hydrogenchloride; sodium hydroxide / water; methanol; tetrahydrofuran / 12 h / 50 °C
  • 19
  • [ 22190-40-5 ]
  • [ 99768-12-4 ]
  • methyl 4-(1-acetyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 100℃; for 10h; 12 To a solution of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (1.0 g, 4.0 mmol), (4-(methoxycarbonyl)phenyl) boronic acid (1.08 g, 6.0 mmol), and Na2CO3 (850 mg, 8.0 mmol) in dioxane/H2O (10/2 mL), was added Pd(PPh3)4 (466 mg, 0.4 mmol). The mixture was stirred at 100 for 10 h. It was then extracted with EA, the combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified by flash chromatography to give methyl 4-(1-acetyl-1,2,3,4 -tetrahydroquinolin-6-yl)benzoate as a white solid (1.25 g, 100%). LC-MS (ESI): m/z (M+H)+ = 310.13.
  • 20
  • [ 22190-40-5 ]
  • tert-butyl 7-(2-amino-5-(bis(4-methoxybenzyl)amino)-6-fluoroquinazolin-7-yl)-8-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate [ No CAS ]
  • 1-[6-[5-amino-6-fluoro-7-(8-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-7-yl)quinazolin-2-yl]amino}-3,4-dihydroquinolin-1(2H)-yl]ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one; tert-butyl 7-(2-amino-5-(bis(4-methoxybenzyl)amino)-6-fluoroquinazolin-7-yl)-8-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate With tripotassium phosphate tribasic; tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′- triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In lithium hydroxide monohydrate; toluene at 110℃; Inert atmosphere; Stage #2: With trifluoroacetic acid In 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran for 2h; 2A.3-2A.4 Steps 3 and 4. Synthesis of Compound 2-7. A mixture of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (29 mg, 0.11 mmol), intermediate I-16 (50 mg, 0.075 mmol), t-BuBrettPhos (15 mg, 0.030 mmol), Pd2(dba)3(6.9 mg, 7.5 μmol), and K3PO4 (32 mg, 0.15 mmol) in toluene (0.75 mL) and water (10 μL) was deoxygenated by bubbling argon for 3 min, then warmed to 110 °C and stirred overnight. After cooling to to RT, filtered and concentrated. Crude reaction residue was dissolved in 1 mL of DCM, 1 mL of TFA, aged for 2 h. After concentration and the crude mixture was purified by reverse phase chromatography (15-70% ACN/water with 0.1% NH4OH) to give the desired product, 2-7.1H NMR (500 MHz, DMSO-d6) δ 9.69 (s, 1H), 9.57 (s, 1H), 7.84 (s, 1H), 7.70 (s, 2H), 7.35 (s, 1H), 6.62 (d, J = 5.7 Hz, 1H), 6.35 (s, 2H), 5.69 (s, 1H), 4.39 - 4.21 (m, 2H), 3.66 (t, J = 6.3 Hz, 2H), 3.38 (s, 2H), 2.69 (s, 2H), 2.14 (s, 3H), 1.94 (s, 3H), 1.86 (s, 2H). MS (EI) calc’d for C27H27FN7O2, [M+H]+, 500; found, 500.
Stage #1: 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one; tert-butyl 7-(2-amino-5-(bis(4-methoxybenzyl)amino)-6-fluoroquinazolin-7-yl)-8-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-1-carboxylate With tripotassium phosphate tribasic; tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′- triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine In lithium hydroxide monohydrate; toluene at 110℃; Inert atmosphere; Stage #2: With trifluoroacetic acid In 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran for 2h; 2A.3-2A.4 Steps 3 and 4. Synthesis of Compound 2-7. A mixture of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one (29 mg, 0.11 mmol), intermediate I-16 (50 mg, 0.075 mmol), t-BuBrettPhos (15 mg, 0.030 mmol), Pd2(dba)3(6.9 mg, 7.5 μmol), and K3PO4 (32 mg, 0.15 mmol) in toluene (0.75 mL) and water (10 μL) was deoxygenated by bubbling argon for 3 min, then warmed to 110 °C and stirred overnight. After cooling to to RT, filtered and concentrated. Crude reaction residue was dissolved in 1 mL of DCM, 1 mL of TFA, aged for 2 h. After concentration and the crude mixture was purified by reverse phase chromatography (15-70% ACN/water with 0.1% NH4OH) to give the desired product, 2-7.1H NMR (500 MHz, DMSO-d6) δ 9.69 (s, 1H), 9.57 (s, 1H), 7.84 (s, 1H), 7.70 (s, 2H), 7.35 (s, 1H), 6.62 (d, J = 5.7 Hz, 1H), 6.35 (s, 2H), 5.69 (s, 1H), 4.39 - 4.21 (m, 2H), 3.66 (t, J = 6.3 Hz, 2H), 3.38 (s, 2H), 2.69 (s, 2H), 2.14 (s, 3H), 1.94 (s, 3H), 1.86 (s, 2H). MS (EI) calc’d for C27H27FN7O2, [M+H]+, 500; found, 500.
  • 21
  • C9H10BrN*C2HF3O2 [ No CAS ]
  • [ 75-36-5 ]
  • [ 22190-40-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran at 23℃; for 1h; Inert atmosphere; 2A.1-2A.2 Steps 1 and 2. Preparation of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one. A solution of tert-butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate, HCl (150 mg, 0.430 mmol) in DCM (2.2 mL) was treated with TFA (0.33 mL, 4.3 mmol). The reaction bubbled and allowed to age at RT for 2 h. The solvent was removed under reduced pressure to give 6-bromo-1,2,3,4-tetrahydroquinoline, TFA. The crude oil was taken up in DCM (2 mL) and added acetyl chloride (31 μL, 0.43 mmol). This was followed by the slow addition of triethylamine (0.18 mL, 1.3 mmol). The reaction was allowed to stir at 23 °C. After 1 h, the reaction was diluted with DCM and added water. The mixture was transferred to a separatory funnel and shaken up vigorously. The organic layer was separated and the organic layer was extracted with DCM (3 x 25 mL). The combined organic layer was washed with brine and then separated. The organic layer was dried over Na2SO4and then concentrated to dryness over reduced pressure. The residue was purified by chromatography on SiO2(gradient of 0-10% MeOH/DCM in 4 g silica gel) to afford 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one. MS (EI) calc’d for C11H13BrNO [M+H]+, 254, 256; found, 254, 256.
With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran at 23℃; for 1h; Inert atmosphere; 2A.1-2A.2 Steps 1 and 2. Preparation of 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one. A solution of tert-butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate, HCl (150 mg, 0.430 mmol) in DCM (2.2 mL) was treated with TFA (0.33 mL, 4.3 mmol). The reaction bubbled and allowed to age at RT for 2 h. The solvent was removed under reduced pressure to give 6-bromo-1,2,3,4-tetrahydroquinoline, TFA. The crude oil was taken up in DCM (2 mL) and added acetyl chloride (31 μL, 0.43 mmol). This was followed by the slow addition of triethylamine (0.18 mL, 1.3 mmol). The reaction was allowed to stir at 23 °C. After 1 h, the reaction was diluted with DCM and added water. The mixture was transferred to a separatory funnel and shaken up vigorously. The organic layer was separated and the organic layer was extracted with DCM (3 x 25 mL). The combined organic layer was washed with brine and then separated. The organic layer was dried over Na2SO4and then concentrated to dryness over reduced pressure. The residue was purified by chromatography on SiO2(gradient of 0-10% MeOH/DCM in 4 g silica gel) to afford 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)ethan-1-one. MS (EI) calc’d for C11H13BrNO [M+H]+, 254, 256; found, 254, 256.
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Additions of Organometallic Reagents • Acetal Formation • Acid-Catalyzed α -Halogenation of Ketones • Acyl Group Substitution • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldehydes May Made by Terminal Alkynes Though Hydroboration-oxidation • Aldol Addition • Aldol Condensation • Alkenes React with Ozone to Produce Carbonyl Compounds • Alkyl Halide Occurrence • Alkylation of Aldehydes or Ketones • Alkylation of an Alkynyl Anion • Alkylation of Enolate Ions • Amide Hydrolysis • Amide Hydrolysis • Amides Can Be Converted into Aldehydes • Amines Convert Acyl Chlorides into Amides • An Alkane are Prepared from an Haloalkane • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Clemmensen Reduction • Complex Metal Hydride Reductions • Conjugated Enone Takes Part in 1,4-Additions • Convert Haloalkanes into Alcohols by SN2 • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of 3-Ketoacids Yields Ketones • Decarboxylation of Substituted Propanedioic • Deoxygenation of the Carbonyl Group • Deprotonation of a Carbonyl Compound at the α -Carbon • Diorganocuprates Convert Acyl Chlorides into Ketones • Dithioacetal Formation • Enamines Can Be Used to Prepare Alkylated Aldehydes • Enol-Keto Equilibration • Enolate Ions Are Protonated to Form ketones • Exclusive 1,4-Addition of a Lithium Organocuprate • Fischer Indole Synthesis • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Furan Hydrolyzes to Dicarbonyl Compounds • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hantzsch Pyridine Synthesis • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • Henry Nitroaldol Reaction • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hiyama Cross-Coupling Reaction • Hofmann Rearrangement • Horner-Wadsworth-Emmons Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydrogenation by Palladium on Carbon Gives the Saturated Carbonyl Compound • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Isomerization of β, γ -Unsaturated Carbonyl Compounds • Ketone Synthesis from Nitriles • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • Lithium Organocuprate may Add to the α ,β -Unsaturated Carbonyl Function in 1,4-Fashion • Mannich Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mercury Ions Catalyze Alkynes to Ketones • Methylation of Ammonia • Methylation of Ammonia • Michael Addition • Oxidation of Alcohols to Carbonyl Compounds • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Phenylhydrazone and Phenylosazone Formation • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reductive Amination • Reductive Amination • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Strecker Synthesis • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Reaction of Alkynyl Anions with Carbonyl Derivatives • The Wittig Reaction • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Williamson Ether Syntheses • Wittig Reaction • Wolff-Kishner Reduction
Historical Records

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; ;