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inquiry4-(2-Bromoethyl)-2-oxoindole CAS No.:120427-96-5 Name: 4-(2-Bromoethyl)-2-oxoindole Synonyms: 4-(2-Bromoethyl)indolin-2-one; 4-(2-Bromoethyl)-1,3-dihydro-2H-indol-2-one Molecular St
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inquiryChemical Name 4-(2-Bromoethyl)-2-oxoindole Synonyms 4-(2'-BROMOETHYL)-1,3-DIHYDRO-2H-INDOLE-2-ONE; CAS No. 120427-96-5 Molecular Formula C10H10BrNO
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4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With sodium hypophosphite; palladium on activated charcoal In ethyl acetate for 0.583333h; Heating; | 95% |
With sodium hypophosphite monohydrate; palladium on activated charcoal In water; ethyl acetate Large scale; | 95% |
With sodium hypophosphite hydrate; palladium 10% on activated carbon In water; ethyl acetate for 1h; Heating / reflux; | 88.97% |
With phosphonic Acid; sodium iodide In ethanol at 70℃; for 5h; Reagent/catalyst; | 86.7% |
2-(2-bromoethyl)benzaldehyde
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / MeONa / methanol / 1 h / 0 °C 2: 53 percent / AcCl, FeCl3 / CH2Cl2 / 3 h / 0 - 5 °C 3: 95 percent / aq. NaH2PO2 / 10percent Pd-C / ethyl acetate / 0.58 h / Heating View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 53 percent / AcCl, FeCl3 / CH2Cl2 / 3 h / 0 - 5 °C 2: 95 percent / aq. NaH2PO2 / 10percent Pd-C / ethyl acetate / 0.58 h / Heating View Scheme |
pyrographite
palladium
4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
In water |
4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
carbon palladium In water | 17.0 g (82%) |
isochromane
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: bromine / water / Irradiation 2: water; methanol / Acidic conditions; Large scale 3: iron(III) chloride / Acidic conditions; Large scale 4: palladium on activated charcoal; sodium hypophosphite monohydrate / water; ethyl acetate / Large scale View Scheme | |
Multi-step reaction with 7 steps 1: zinc(II) chloride / dichloromethane / Reflux 2: hexamethylenetetramine; acetic acid / ethanol; water 3: N-butylamine; acetic acid; nitromethane / methanol / 20 °C 4: iron(III) chloride / dichloromethane / 0 - 5 °C 5: hydrazine hydrate; palladium 10% on activated carbon / methanol 6: sodium hydroxide; water / methanol / Reflux 7: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
1-Bromoisochromane
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: water; methanol / Acidic conditions; Large scale 2: iron(III) chloride / Acidic conditions; Large scale 3: palladium on activated charcoal; sodium hypophosphite monohydrate / water; ethyl acetate / Large scale View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: iron(III) chloride / Acidic conditions; Large scale 2: palladium on activated charcoal; sodium hypophosphite monohydrate / water; ethyl acetate / Large scale View Scheme |
4-[2-(benzoyloxy)ethyl]-3-chloro-1,3-dihydro-2H-indolin-2-one
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrazine hydrate; palladium 10% on activated carbon / methanol 2: sodium hydroxide; water / methanol / Reflux 3: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
4-(2-benzoyloxyethyl)-1,3-dihydro-2H-indolin-2-one
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide; water / methanol / Reflux 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; |
2-(2-methyl-3-nitrophenyl)acetic acid
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: borane-THF / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 8 h / 20 °C / Inert atmosphere 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere 3.2: 8 h / 20 °C / Inert atmosphere 4.1: sodium hydroxide / tetrahydrofuran / 0.17 h / 0 °C 4.2: 1 h / 20 °C / pH 1.5 5.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C 6.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
2-[2-(chloromethyl)phenyl]ethylbenzoate
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: hexamethylenetetramine; acetic acid / ethanol; water 2: N-butylamine; acetic acid; nitromethane / methanol / 20 °C 3: iron(III) chloride / dichloromethane / 0 - 5 °C 4: hydrazine hydrate; palladium 10% on activated carbon / methanol 5: sodium hydroxide; water / methanol / Reflux 6: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
2-(2-methyl-3-nitrophenyl)ethyl alcohol
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 8 h / 20 °C / Inert atmosphere 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere 2.2: 8 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / tetrahydrofuran / 0.17 h / 0 °C 3.2: 1 h / 20 °C / pH 1.5 4.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C 5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
1-[(2-methyl-3-nitrophenethyloxy)methyl]benzene
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere 1.2: 8 h / 20 °C / Inert atmosphere 2.1: sodium hydroxide / tetrahydrofuran / 0.17 h / 0 °C 2.2: 1 h / 20 °C / pH 1.5 3.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C 4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
ethyl 3-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]-2-oxopropanoate
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydroxide / tetrahydrofuran / 0.17 h / 0 °C 1.2: 1 h / 20 °C / pH 1.5 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C 3.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
2-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]acetic acid
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethanol / 5 h / 20 °C 2: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
benzoic acid (2-formyl)phenethyl ester
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: N-butylamine; acetic acid; nitromethane / methanol / 20 °C 2: iron(III) chloride / dichloromethane / 0 - 5 °C 3: hydrazine hydrate; palladium 10% on activated carbon / methanol 4: sodium hydroxide; water / methanol / Reflux 5: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
benzoic acid (2-(2-nitroethenyl))phenethyl ester
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: iron(III) chloride / dichloromethane / 0 - 5 °C 2: hydrazine hydrate; palladium 10% on activated carbon / methanol 3: sodium hydroxide; water / methanol / Reflux 4: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C View Scheme |
sodium acetate
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
4-(2-acetoxyethyl)-1,3-dihydro-2H-indolin-2-one
Conditions | Yield |
---|---|
In ethanol; water for 24h; Heating; | 89% |
di-n-propylamine
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
A
ropinirole hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water Large scale; | A 57% B 38% |
di-n-propylamine
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
ropinirole hydrochloride
Conditions | Yield |
---|---|
Stage #1: di-n-propylamine; 4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one In water; acetonitrile at 65 - 70℃; for 1.25h; Stage #2: With hydrogenchloride In water pH=2; | 50% |
propylamine
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Reflux; | A 35% B 45% |
di-n-propylamine
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
A
Ropinirole
Conditions | Yield |
---|---|
In water for 2.5h; Heating; | A n/a B 38% |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Ropinirole
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C 4: H2O / 2 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C 4: H2O / 2 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C 4: H2O / 2 h / Heating View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C 4: H2O / 2 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C 4: H2O / 2 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C 4: H2O / 2 h / Heating View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl methanesulfonate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
2-(2'-oxo-2,3-dihydro-4-indolyl)ethyl benzenesulphonate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C View Scheme |
4-(2'-bromoethyl)-1,3-dihydro-2H-indol-2-one
2-(2-oxo-2,3-dihydro-1H-indol-4-yl)ethyl-4-methylbenzene-1-sulfonate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme |
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