6-chloroisatin
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With titanium tetrachloride; zinc In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; | 88% |
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 0.5 h / Heating 2: Na / ethanol / Heating View Scheme | |
With sodium ethanolate; hydrazine hydrate In ethanol |
methyl 2-(4-chloro-2-nitrophenyl)acetate
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With iron In acetic acid at 100℃; for 1h; | 87% |
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / 2280.15 Torr / Sealed tube 2: ethyl acetate / 6 h / Reflux; Molecular sieve View Scheme |
(4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With hydrogenchloride; tin In ethanol Heating; | 79% |
dimethyl (4-chloro-2-nitrophenyl)malonate
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With iron; acetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 25 - 105℃; Large scale; | 75% |
Stage #1: dimethyl (4-chloro-2-nitrophenyl)malonate With hydrogenchloride; water In methanol at 20 - 95℃; Large scale; Stage #2: With tin In methanol at 45 - 95℃; Large scale; | 75% |
Stage #1: dimethyl (4-chloro-2-nitrophenyl)malonate With lithium chloride In dimethyl sulfoxide at 100℃; for 3h; Stage #2: With iron; acetic acid at 100℃; for 1h; |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With hydrogen; acetic acid; Pt/C In water | 71% |
4-chloro-2-nitro-phenylacetic acid
A
6-chloro-1-hydroxy-indolin-2-one
B
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Stage #1: 4-chloro-2-nitro-phenylacetic acid With 1,10-Phenanthroline; platinum on carbon; hydrogen In ethanol at 20℃; under 7500.75 Torr; Flow reactor; Green chemistry; Stage #2: With acetic acid In ethanol at 20℃; Green chemistry; | A 63% B n/a |
Conditions | Yield |
---|---|
With silver(I) acetate; palladium diacetate; trifluoroacetic acid at 120℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; regioselective reaction; | 53% |
2-chloro-N-(3-chlorophenyl)acetamide
A
4-chloroindolin-2-one
B
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With aluminium trichloride 1. 50-60 deg C, 10 min; 2. 150-160 deg C, 2 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With aluminium trichloride Product distribution; 50-60 deg C, 10 min; 150-160 deg C, 2 h; |
6-chloroisatin 3-hydrazone
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With sodium In ethanol Heating; Yield given; | |
With potassium tert-butylate In ethanol for 2h; Reflux; Inert atmosphere; |
2,5-dichloronitrobenzene
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: tBuOK / dimethylformamide / 0.17 h / 90 °C 1.2: dimethylformamide / 2 h / 90 °C 2.1: LiCl / dimethylsulfoxide / 3 h / 100 °C 2.2: acetic acid; iron / 1 h / 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: 84 percent / NaH / dimethylsulfoxide / 100 °C 2: 79 percent / Sn, HCl / ethanol / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 1) NaH / 1) DMSO, 100 deg C, 40 min, 2a) RT, 30 min, 2b) 100 deg C, 1 h 2: 69 percent / LiCl / dimethylsulfoxide; H2O / 3 h / 100 °C 3: 87 percent / Fe powder / acetic acid / 1 h / 100 °C View Scheme |
3-chloro-aniline
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 62 percent / benzene / Heating 2: AlCl3 / 50-60 deg C, 10 min; 150-160 deg C, 2 h View Scheme | |
Multi-step reaction with 4 steps 1.1: hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate / water / 60 - 70 °C 2.1: sulfuric acid / 80 - 90 °C 3.1: sulfuric acid; water 4.1: hydrazine hydrate / ethanol / Reflux 4.2: Reflux View Scheme | |
Multi-step reaction with 4 steps 1: sodium sulfate; sulfuric acid; hydroxylamine hydrochloride / water / 0.5 h / 130 °C 2: sulfuric acid / 1 h / 50 - 70 °C 3: hydrazine hydrate / ethanol / 0.5 h / Inert atmosphere; Reflux 4: potassium tert-butylate / ethanol / 2 h / Reflux; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C / Inert atmosphere 2: palladium diacetate; silver(I) acetate; trifluoroacetic acid / 24 h / 120 °C / Sealed tube; Inert atmosphere; Schlenk technique View Scheme |
4-chloro-2-nitro-phenylacetic acid
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Stage #1: 4-chloro-2-nitro-phenylacetic acid With iron; acetic acid In methanol at 50 - 75℃; for 1h; Stage #2: With hydrogenchloride In methanol; water at 20 - 25℃; | |
Multi-step reaction with 2 steps 1: sodium dithionite / ethanol / 4 h / 40 - 45 °C 2: hydrogenchloride / ethanol / 2 h / 70 - 75 °C / pH 2 - 2.5 View Scheme |
6-chloro-3-iminoindolin-2-one
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid; water 2.1: hydrazine hydrate / ethanol / Reflux 2.2: Reflux View Scheme |
Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid / 80 - 90 °C 2.1: sulfuric acid; water 3.1: hydrazine hydrate / ethanol / Reflux 3.2: Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sulfuric acid / 1 h / 50 - 70 °C 2: hydrazine hydrate / ethanol / 0.5 h / Inert atmosphere; Reflux 3: potassium tert-butylate / ethanol / 2 h / Reflux; Inert atmosphere View Scheme |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tris(bipyridine)ruthenium(II) dichloride hexahydrate; oxygen / 20 °C / Irradiation 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 °C / 2280.15 Torr / Sealed tube 3: ethyl acetate / 6 h / Reflux; Molecular sieve View Scheme |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
In ethyl acetate for 6h; Reflux; Molecular sieve; |
(2-amino-4-chlorophenyl)acetic acid
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 70 - 75℃; for 2h; pH=2 - 2.5; |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 1 h / 0 - 40 °C / pH 6 - 6.5 2: sodium dithionite / ethanol / 4 h / 40 - 45 °C 3: hydrogenchloride / ethanol / 2 h / 70 - 75 °C / pH 2 - 2.5 View Scheme |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / ethanol / 1 h / 0 - 40 °C / pH 6 - 6.5 2: sodium dithionite / ethanol / 4 h / 40 - 45 °C 3: hydrogenchloride / ethanol / 2 h / 70 - 75 °C / pH 2 - 2.5 View Scheme |
6-chloro-2-oxindole
3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one
Conditions | Yield |
---|---|
With pyridinium hydrobromide perbromide In water; tert-butyl alcohol at 20℃; for 3.5h; | 100% |
With pyridinium perbromide hydrobromide In water; tert-butyl alcohol for 16h; | 99% |
With copper(ll) bromide In ethyl acetate at 80℃; |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
In chloroform Heating; | 100% |
Conditions | Yield |
---|---|
With piperidine In methanol at 0 - 20℃; for 24h; | 97% |
6-chloro-2-oxindole
2-fluoro-3-chlorobenzaldehyde
6-chloro-3-[1-(3-chloro-2-fluorophenyl)-meth-(E)-ylidene]-1,3-dihydroindol-2-one
Conditions | Yield |
---|---|
With piperidine In methanol at 20℃; Reflux; | 96% |
With piperidine for 6h; Reflux; | 95% |
With piperidine for 6h; Reflux; | 95% |
Conditions | Yield |
---|---|
With H4[PVMo11O40] suppoted montmorillonite K-10 clay In neat (no solvent) at 100℃; for 1h; Green chemistry; | 96% |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at -10 - 20℃; for 3h; | 95.8% |
With N-Bromosuccinimide In acetonitrile at -10 - 20℃; for 3h; | 95.8% |
With N-Bromosuccinimide In acetonitrile at -10 - 20℃; for 5h; | 4.5 g |
6-chloro-2-oxindole
3-Chlorobenzaldehyde
E/Z-6-chloro-3-[1-(3-chlorophenyl)methylidene]-1,3-dihydroindol-2-one
Conditions | Yield |
---|---|
With pyrrolidine In methanol at 70℃; for 3h; | 95% |
With pyrrolidine In methanol at 70℃; for 3h; | 95% |
With pyrrolidine In methanol at 70℃; for 3h; | 95% |
6-chloro-2-oxindole
acetone
6-chloro-3-(propan-2-ylidene)indolin-2-one
Conditions | Yield |
---|---|
With morpholine for 16h; Knoevenagel Condensation; Reflux; | 95% |
With piperidine In ethanol at 23℃; for 4h; | |
With piperidine at 120℃; for 0.166667h; Microwave irradiation; Inert atmosphere; | |
With piperidine In ethanol at 23℃; for 4h; Inert atmosphere; |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With zinc trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 21℃; for 4h; | 95% |
6-chloro-2-oxindole
2-fluoro-3-chlorobenzaldehyde
(3E/Z)-6-chloro-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With piperidine In ethanol at 80℃; for 2h; Inert atmosphere; | 94% |
With piperidine In methanol at 50℃; for 3h; | 89% |
With piperidine In ethanol for 8h; Inert atmosphere; Reflux; |
6-chloro-2-oxindole
acetic anhydride
1,3-diacetyl-6-chloro-1H-indol-2-yl acetate
Conditions | Yield |
---|---|
With dmap at 150℃; for 1h; | 93% |
With dmap at 150℃; for 1h; | 93% |
6-chloro-2-oxindole
phenyl chloroformate
6-chloro-2-phenoxycarbonyloxy-indole-1-carboxylic acid phenyl ester
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Acylation; | 92% |
With triethylamine In tetrahydrofuran |
6-chloro-2-oxindole
6-chloroindoline-2-thione
Conditions | Yield |
---|---|
With tetraphosphorus decasulfide; sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 4h; | 92% |
Stage #1: 6-chloro-2-oxindole With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; | |
Stage #1: 6-chloro-2-oxindole With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; | |
With Lawessons reagent In tetrahydrofuran for 24h; Reflux; |
6-chloro-2-oxindole
2-chloropropionyl chloride
6-chloro-5-(3-chloro-propionyl)-1,3-dihydro-indol-2-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In carbon disulfide at 20℃; for 3h; Heating / reflux; | 92% |
6-chloro-2-oxindole
6-chloro-2-oxindole-3-thione S-oxide
Conditions | Yield |
---|---|
With thionyl chloride In acetonitrile at 25 - 30℃; for 0.166667h; | 92% |
3-bromo-2-fluorobenzaldehyde
6-chloro-2-oxindole
(E/Z)-3-(3-bromo-2-fluoro-benzylidene)-6-chloro-1,3-dihydro-indol-2-one
Conditions | Yield |
---|---|
With piperidine In methanol at 80℃; for 2h; | 92% |
6-chloro-2-oxindole
3-chloro-5-fluorobenzaldehyde
(3E/Z)-6-chloro-3-(3-chloro-5-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With piperidine In methanol at 80℃; for 2h; | 92% |
6-chloro-2-oxindole
chloroacetyl chloride
6-chloro-5-(2-chloroacetyl) indolin-2-one
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 30℃; for 24h; Inert atmosphere; | 90.6% |
With aluminium trichloride In carbon disulfide | |
With aluminum (III) chloride In dichloromethane at 0 - 45℃; for 14h; Heating / reflux; |
6-chloro-2-oxindole
4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester
E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With piperidine In methanol at 100℃; for 3h; | 90% |
6-chloro-2-oxindole
p-Chlorothiophenol
Conditions | Yield |
---|---|
With iron(III) chloride; potassium carbonate In dimethyl sulfoxide at 50℃; for 1.5h; Green chemistry; | 90% |
6-chloro-2-oxindole
malononitrile
2-(6-chloro-2-oxoindolin-3-ylidene)malononitrile
Conditions | Yield |
---|---|
With iron(III) chloride hexahydrate; oxygen In N,N-dimethyl-formamide at 50℃; for 5h; Green chemistry; | 90% |
6-chloro-2-oxindole
6-chloroisatin
Conditions | Yield |
---|---|
With oxygen; copper(II) acetate monohydrate; potassium carbonate In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 0.5h; | 89% |
Stage #1: 6-chloro-2-oxindole With pyridinium perbromide hydrobromide Stage #2: With methanol; water | 85% |
Multi-step reaction with 2 steps 1: CuBr2 / ethyl acetate / 80 °C 2: water / methanol / 2 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 99 percent / pyridine*HBr*Br2 / 2-methyl-propan-2-ol; H2O / 16 h 2: 57 percent / H2O / methanol / 50 h / Heating View Scheme |
Conditions | Yield |
---|---|
Stage #1: 6-chloro-2-oxindole; azulene With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 2.5h; Vilsmeier-Haack type arylation; Stage #2: With potassium carbonate In dichloromethane; water | 89% |
6-chloro-2-oxindole
4-methyl-benzaldehyde
(E)-3-(4-methylbenzylidene)-6-chloroindolin-2-one
Conditions | Yield |
---|---|
With piperidine In ethanol for 3h; Reflux; | 89% |
6-chloro-2-oxindole
Conditions | Yield |
---|---|
With pyrrolidine In isopropyl alcohol at 90℃; for 48h; | 88% |
6-chloro-2-oxindole
4-(Methylthio)benzaldehyde
(E)-3-(4-(methylthio)benzylidene)-6-chloroindolin-2-one
Conditions | Yield |
---|---|
With piperidine In ethanol for 3h; Reflux; | 88% |
Conditions | Yield |
---|---|
In ethanol | 87% |
Conditions | Yield |
---|---|
at 130℃; for 7h; | 87% |
With sodium carbonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
The CAS register number of 6-Chloroindol-2(3H)-one is 56341-37-8. It also can be called as 2H-Indol-2-one,6-chloro-1,3-dihydro- and the systematic name about this chemical is 6-chloro-1,3-dihydro-2H-indol-2-one. The molecular formula about this chemical is C8H6ClNO and the molecular weight is 167.59. It belongs to the following product categories, such as Blocks; IndolesOxindoles; Indole/indoline/oxindole; Indole and Indoline; Starting Raw Materials & Intermediates; Heterocycles; Indoles and derivatives; Indole; Indoles and so on. This chemical is an important pharmaceutical intermediate to product Ziprasidone. If you want to store this chemical, please keep it in a tighely closed container, store it in a dry, cool place and ensure workplace has good ventilation.
Physical properties about 6-Chloroindol-2(3H)-one are: (1)ACD/LogP: 2.17; (2)ACD/LogD (pH 5.5): 2.17; (3)ACD/LogD (pH 7.4): 2.17; (4)ACD/BCF (pH 5.5): 26.03; (5)ACD/BCF (pH 7.4): 26.03; (6)ACD/KOC (pH 5.5): 358.75; (7)ACD/KOC (pH 7.4): 358.75; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Polar Surface Area: 20.31Å2; (11)Index of Refraction: 1.601; (12)Molar Refractivity: 42.18 cm3; (13)Molar Volume: 123 cm3; (14)Polarizability: 16.72x10-24cm3; (15)Surface Tension: 47.5 dyne/cm; (16)Enthalpy of Vaporization: 57.14 kJ/mol; (17)Boiling Point: 329 °C at 760 mmHg; (18)Vapour Pressure: 0.000183 mmHg at 25°C.
Preparation: this chemical can be prepared by (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester. This reaction will need reagent Sn, HCl and solvent ethanol at heating. The yield is about 79%.
Uses of 6-Chloroindol-2(3H)-one: it can be used to produce 3,3-dibromo-6-chloro-1,3-dihydro-indol-2-one. This reaction will need reagent pyridine*HBr*Br2 and solvent 2-methyl-propan-2-ol, H2O with reaction time of 16 hours. The yield is about 99%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed and it is irritating to eyes, respiratory system and skin, it may cause sensitization by skin contact. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc2c(c1)NC(=O)C2
(2)InChI: InChI=1/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)
(3)InChIKey: CENVPIZOTHULGJ-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)
(5)Std. InChIKey: CENVPIZOTHULGJ-UHFFFAOYSA-N
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