3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Stage #1: 3-[2-(3-chlorophenyl)ethyl]-2-pyridine-carbonitrile With trifluorormethanesulfonic acid at 60℃; for 1h; Stage #2: With hydrogenchloride In water at 20℃; for 1h; Heating / reflux; | 94% |
With PPA at 200℃; | 45% |
With PPA Heating; |
3-[2-(5-chloro-2-iodo-phenyl)-ethyl]-pyridine-2-carboxylic acid methyl-phenyl-amide
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.166667h; | 91% |
With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.166667h; | 78% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With water at 0 - 35℃; for 25 - 35h; | 76.4% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In carbon disulfide | 40% |
2-iodoyl-3,5-dichlorobenzoic acid
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 121 g / (MeO)3B; BH3*Me2S / tetrahydrofuran / 18 h / 20 °C 2.1: PPh3; Br2 / acetonitrile / 1 h / 20 °C 3.1: LDA; t-BuOMe / various solvent(s); tetrahydrofuran / -30 - 0 °C 4.1: NaH / dimethylformamide / 1 h / 0 °C 4.2: 10 g / dimethylformamide / 0.25 h / 0 °C 5.1: 91 percent / n-BuLi / tetrahydrofuran; cyclohexane / 0.17 h / -78 °C View Scheme |
5-chloro-2-iodobenzyl alcohol
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: PPh3; Br2 / acetonitrile / 1 h / 20 °C 2.1: LDA; t-BuOMe / various solvent(s); tetrahydrofuran / -30 - 0 °C 3.1: NaH / dimethylformamide / 1 h / 0 °C 3.2: 10 g / dimethylformamide / 0.25 h / 0 °C 4.1: 91 percent / n-BuLi / tetrahydrofuran; cyclohexane / 0.17 h / -78 °C View Scheme |
2-(bromomethyl)-4-chloro-1-iodobenzene
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: LDA; t-BuOMe / various solvent(s); tetrahydrofuran / -30 - 0 °C 2.1: NaH / dimethylformamide / 1 h / 0 °C 2.2: 10 g / dimethylformamide / 0.25 h / 0 °C 3.1: 91 percent / n-BuLi / tetrahydrofuran; cyclohexane / 0.17 h / -78 °C View Scheme |
3-[2-(5-chloro-2-iodo-phenyl)-ethyl]-pyridine-2-carboxylic acid phenylamide
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 1 h / 0 °C 1.2: 10 g / dimethylformamide / 0.25 h / 0 °C 2.1: 91 percent / n-BuLi / tetrahydrofuran; cyclohexane / 0.17 h / -78 °C View Scheme |
N-tert-butyl-3-methylpyridine-2-carboxamide
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) THF, -40 deg C 2: POCl3 / Heating 3: PPA / Heating View Scheme |
3-<2-(3-chlorophenyl)ethyl>-N-(1,1-dimethylethyl)-2-pyridinecarboxamide
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: POCl3 / Heating 2: PPA / Heating View Scheme |
1-Chloro-3-chloromethyl-benzene
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) THF, -40 deg C 2: POCl3 / Heating 3: PPA / Heating View Scheme |
3-[2-(3-Chlorophenyl)ethyl]-pyridine-2-carboxylic acid hydrochloride
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Stage #1: 3-[2-(3-Chlorophenyl)ethyl]-pyridine-2-carboxylic acid hydrochloride With thionyl chloride at 30 - 60℃; Stage #2: aluminum (III) chloride In 1,2-dichloro-ethane at -5 - 20℃; |
N-phenyl-3-[2-(3-chlorophenyl)ethyl]-2-pyridine carboxamide
phosphorus pentachloride
pyrographite
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
aluminium trichloride In hexane; dichloromethane; toluene | 44.2 g (61%) |
N-phenyl-3-[2-(3-chlorophenyl)ethyl]-2-pyridine carboxamide
pyrographite
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With trichlorophosphate In hexane; water; chlorobenzene | 44.1 g (50.8%) |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 4 h / 760.05 Torr 2: sodium hydroxide; water / ethanol / 48 h 3: thionyl chloride 4: aluminum (III) chloride / carbon disulfide View Scheme |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; water / ethanol / 48 h 2: thionyl chloride 3: aluminum (III) chloride / carbon disulfide View Scheme |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride 2: aluminum (III) chloride / carbon disulfide View Scheme |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 48 h / 760.05 Torr 2: sodium hydroxide; water / ethanol / 5 h / Reflux 3: thionyl chloride 4: aluminum (III) chloride / carbon disulfide View Scheme |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydroxide; water / ethanol / 5 h / Reflux 2: thionyl chloride 3: aluminum (III) chloride / carbon disulfide View Scheme |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With water; sodium hydroxide In tetrahydrofuran at 80 - 90℃; pH=10-11; |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
8-Chloro-6,11-Dihydro-11-Hydroxy-5H-Benzo[5,6]-Cyclohepta[1,2-b]Pyridine
Conditions | Yield |
---|---|
Stage #1: 8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; Stage #2: With hydrogenchloride In methanol; water | 100% |
With sodium tetrahydroborate In methanol at 10 - 20℃; for 2.75h; | 96.9% |
With sodium tetrahydroborate In methanol a) 0 deg C, 2.5 h, b) from 0 deg C to 25 deg C, 1 h; |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
(1-methyl-4-piperidyl)magnesium chloride
8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol
Conditions | Yield |
---|---|
In tetrahydrofuran Reflux; | 95% |
With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 0℃; for 2h; Inert atmosphere; | 90% |
In tetrahydrofuran at -95 - -15℃; for 2 - 3h; | 71.1% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
5,6-Dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; triethylamine In tetrahydrofuran at 20℃; for 24h; | 89% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
diethyl N-ethoxycarbonylpiperidine-4-phosphonate
Conditions | Yield |
---|---|
Stage #1: diethyl N-ethoxycarbonylpiperidine-4-phosphonate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -25 - -5℃; for 2h; Stage #2: 8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one In tetrahydrofuran; hexane at -25 - -20℃; for 2h; | 82% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
1-methylpiperidin-2-one
3-(8-Chloro-11-hydroxy-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-1-methyl-piperidin-2-one
Conditions | Yield |
---|---|
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane 1.) -78 deg C, 30 min; -78 deg C to -5 deg C, 60 min, 2.) -78 deg C, 1 h; -78 deg C to -10 deg C, 1 h; | 76% |
2-(4-formylphenyl)pyridine
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 10h; Reflux; | 75% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
methyl 4-formylbenzoate
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 10h; Reflux; | 75% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
4-phenylsulfanyl-benzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 8h; Reflux; | 74% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Phenanthrene-9-carboxaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 7h; Reflux; | 74% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
triethyl phosphite
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 20℃; for 24h; | 73.8% |
4-chloro-1-methylpiperidine
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
8-chloro-6,11-dihydro-11-(1-methyl-4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ol
Conditions | Yield |
---|---|
Stage #1: 4-chloro-1-methylpiperidine With magnesium; ethylene dibromide In tetrahydrofuran at 20 - 48℃; Stage #2: 8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one In tetrahydrofuran at -80 - -70℃; for 2 - 3h; Product distribution / selectivity; | 73.6% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
4-cyanobenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 6h; Reflux; | 73% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
2,6-dibromobenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 6h; Reflux; | 73% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
4-styrylbenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 8h; Reflux; | 72% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
9H-fluorene-2-carbaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 6h; Reflux; | 71% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
N-(4-formylphenyl)carbazole
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 10h; Reflux; | 70% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
para-methanesulfonylbenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 10h; Reflux; | 70% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
6-fluorochromone-3-carboxaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 8h; Reflux; | 70% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
2,6-dichlorobenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 6h; Reflux; | 69% |
1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 8h; Reflux; | 68% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
4-(Methylthio)benzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 7h; Reflux; | 68% |
4-benzooxazol-2-yl-benzaldehyde
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 7h; Reflux; | 68% |
2,2'-bithiophene-5-carboxaldehyde
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 10h; Reflux; | 67% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
4-(diphenylamino)benzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 10h; Reflux; | 66% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
phosphorous acid trimethyl ester
Conditions | Yield |
---|---|
With phosphoric acid In chloroform at 20℃; for 12h; | 65% |
8-chloro-5,6-dihydro-11H-Benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid for 7h; Reflux; | 65% |
Molecular structure of 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (CAS NO.31251-41-9) is:
Product Name: 8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
CAS Registry Number: 31251-41-9
Systematic Name: 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one
Empirical Formula: C14H10ClNO
Molecular Weight: 243.6883
Melting Point: 90-92°C
Index of Refraction: 1.632
Molar Refractivity: 66.136 cm3
Molar Volume: 185.481 cm3
Surface Tension: 53.838 dyne/cm
Density: 1.314 g/cm3
Flash Point: 216.042 °C
Enthalpy of Vaporization: 68.959 kJ/mol
Boiling Point: 433.614 °C at 760 mmHg
Product Categories: Aromatics Compounds;Aromatics;Heterocycles;Intermediates
8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (CAS NO.31251-41-9) can be used as loratadine intermediate.
Hazard Codes: Xi
8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one , its cas register number is 31251-41-9. It also can be called 8-Chloro-10,11-Dihydro-4-Aza-5h-Dibenzo-(A,D)Cycloheptan-5-One ; 8-Chloro-5,6-Dihydro-11h-Benzo-(5,6)-Cyclohepta-(1,2-B)-Pyrimidine-11-On ; 8-Chloro-10,11-dihydro-4-aza-5 ; 4-Aza-8-chloro-10,11-dihydro-5H-benzo[a,d]cyclo-5-heptanone .It is a yellow solid.
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