56341-37-8

Basic information

• Product Name: 6-Chlorooxindole
• Synonyms: 6-Chloro-1,3-dihydroindole-2-one;6-Chlorooxindole,98%;6-Chloro-1,3-dihvdro-indol-2-one;6-Chloro-2-oxindole 98%;6-chloro indole ketone;6-Chloroindolin-2-one, 6-Chloro-1,3-dihydro-2H-indol-2-one;1H-indol-6-yl hypochlorite;6-chloroindolin-2-one
• CAS NO: 56341-37-8
• Molecular Formula: C₈H₆ClNO
• Molecular Weight: 167.59
• EINECS: 1312995-182-4
• Product Categories: Indole and Indoline;Starting Raw Materials & Intermediates;Heterocycles;Indoles and derivatives;Indole;Indoles;blocks;IndolesOxindoles;Indole/indoline/oxindole
• Mol File: 56341-37-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 195-199 °C(lit.)
• Boiling Point: 329 °C at 760 mmHg
• Flash Point: 152.8 °C
• Appearance: Off-white to tan crystalline powder
• Density: 1.362 g/cm³
• Vapor Pressure: 0.000183mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Dimethylformamide
• PKA: 13.39±0.20(Predicted)
• CAS DataBase Reference: 6-Chlorooxindole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chlorooxindole(56341-37-8)
• EPA Substance Registry System: 6-Chlorooxindole(56341-37-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43-36/37/38
• Safety Statements: 37/39-36-26
• WGK Germany: 3
• Hazardous Substances Data: 56341-37-8(Hazardous Substances Data)

Usage

Preparation

STEP A: 3-(2-nitro-4-chlorophenyl)pyruvic acid To a cooled mixture prepared by adding 13.6 g. of sodium to 300 ml. of ethanol is added a solution of 100 g. of 4-chloro-2-nitrotoluene and 84 g of diethyloxalate in 150 ml of ethanol while maintaining the temperature below 20℃. The resulting mixture is refluxed for one hour, cooled, 400 ml. of water added and the resulting mixture refluxed for 90 minutes. The ethanol is then evaporated to a small volume and the resulting precipi tate containstan and black material and the black mate rial is mechanically separated and discarded and the remainder (filtrate plus tan precipitate) used in the next step.?STEP B: 4-chloro-2-nitro-phenylacetic acid The filtrate of Step A, above, is adjusted to pH 8-9 with 2 N sodium hydroxide and is heated at 35-40℃. while adding a 3-6% aqueous hydrogen peroxide solution until samples no longer turn dark on treatment with 2N sodium hydroxide. The tan precipitate is suspended in 1500 ml of water, adjusted to pH 8-9 and similarly treated with aqueous hydrogen peroxide. The combined reaction mixtures are then acidified with concentrated hydrochloride acid to obtain a precipitate which are re covered by filtration, washed 3 times with water and dried in vacuo. The crude product (mp 145-150° C) is recrystallized from ether to obtain 4-chloro-2-nitro phenylacetic acid, m.p. 156-159℃.?STEP C: The product of Step B, above, is subjected to reductive cyclization analogously to Step B of Example 1 to obtain 6-chloro-oxindole, m.p. 185-189℃.

InChI:InChI=1/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)

Synthetic route

6-chloroisatin (6341-92-0) → 6-chloro-2-oxindole (56341-37-8)

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 (147124-37-6) → 6-chloro-2-oxindole (56341-37-8)

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 (10565-16-9) → 6-chloro-2-oxindole (56341-37-8)

Conditions	Yield
With hydrogenchloride; tin In ethanol Heating;	79%

dimethyl (4-chloro-2-nitrophenyl)malonate (147124-32-1) → 6-chloro-2-oxindole (56341-37-8)

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;

dimethyl 4-chloro-2-nitrophenyl malonate → 6-chloro-2-oxindole (56341-37-8)

Conditions	Yield
With hydrogen; acetic acid; Pt/C In water	71%

4-chloro-2-nitro-phenylacetic acid (37777-71-2) → 6-chloro-1-hydroxy-indolin-2-one (28230-26-4) + 6-chloro-2-oxindole (56341-37-8)

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

3-Chloroacetanilide (588-07-8) + ethyl iodoacetae (623-48-3) → 6-chloro-2-oxindole (56341-37-8)

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 (2564-05-8) → 4-chloroindolin-2-one (20870-77-3) + 6-chloro-2-oxindole (56341-37-8)

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 (879-32-3) → 6-chloro-2-oxindole (56341-37-8)

Conditions	Yield
With sodium In ethanol Heating; Yield given;
With potassium tert-butylate In ethanol for 2h; Reflux; Inert atmosphere;

2,5-dichloronitrobenzene (89-61-2) → 6-chloro-2-oxindole (56341-37-8)

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 (108-42-9) → 6-chloro-2-oxindole (56341-37-8)

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 (37777-71-2) → 6-chloro-2-oxindole (56341-37-8)

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 (1261152-95-7) → 6-chloro-2-oxindole (56341-37-8)

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 (17122-55-3) → 6-chloro-2-oxindole (56341-37-8)

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

2-nitro-4-chlorobenzene diazonium tetrafluoroborate → 6-chloro-2-oxindole (56341-37-8)

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

methyl 2-(2-amino-4-chlorophenyl)acetate → 6-chloro-2-oxindole (56341-37-8)

Conditions	Yield
In ethyl acetate for 6h; Reflux; Molecular sieve;

(2-amino-4-chlorophenyl)acetic acid (177985-31-8) → 6-chloro-2-oxindole (56341-37-8)

Conditions	Yield
With hydrogenchloride In ethanol at 70 - 75℃; for 2h; pH=2 - 2.5;

2-(4-chloro-2-nitrophenyl)malonate potassium → 6-chloro-2-oxindole (56341-37-8)

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

2-(4-chloro-2-nitrophenyl)malonate sodium → 6-chloro-2-oxindole (56341-37-8)

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 (56341-37-8) → 3,3-Dibromo-6-chloro-1,3-dihydro-indol-2-one (215959-30-1)

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 (56341-37-8) + Me2NCH(OR)2 → 6-Chloro-3-[1-dimethylamino-meth-(Z)-ylidene]-1,3-dihydro-indol-2-one

Conditions	Yield
In chloroform Heating;	100%

6-chloro-2-oxindole (56341-37-8) + methyl 2-oxobutanoate (3952-66-7) → C13H14ClNO4

Conditions	Yield
With piperidine In methanol at 0 - 20℃; for 24h;	97%

6-chloro-2-oxindole (56341-37-8) + 2-fluoro-3-chlorobenzaldehyde (85070-48-0) → 6-chloro-3-[1-(3-chloro-2-fluorophenyl)-meth-(E)-ylidene]-1,3-dihydroindol-2-one (908027-64-5)

Conditions	Yield
With piperidine In methanol at 20℃; Reflux;	96%
With piperidine for 6h; Reflux;	95%
With piperidine for 6h; Reflux;	95%

6-chloro-2-oxindole (56341-37-8) + salicylaldehyde (90-02-8) → C15H8ClNO

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 (56341-37-8) → 5-bromo-6-chloro-1,3-dihydro-2H-indol-2-one

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 (56341-37-8) + 3-Chlorobenzaldehyde (587-04-2) → E/Z-6-chloro-3-[1-(3-chlorophenyl)methylidene]-1,3-dihydroindol-2-one (387344-30-1)

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 (56341-37-8) + acetone (67-64-1) → 6-chloro-3-(propan-2-ylidene)indolin-2-one (1374606-24-2)

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 (56341-37-8) + diphenyl(vinyl)sulfonium trifluoromethanesulfonate → 6'-chloro-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2'-one

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 (56341-37-8) + 2-fluoro-3-chlorobenzaldehyde (85070-48-0) → (3E/Z)-6-chloro-3-(3-chloro-2-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one (897365-76-3)

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 (56341-37-8) + acetic anhydride (108-24-7) → 1,3-diacetyl-6-chloro-1H-indol-2-yl acetate (1195737-73-5)

Conditions	Yield
With dmap at 150℃; for 1h;	93%
With dmap at 150℃; for 1h;	93%

6-chloro-2-oxindole (56341-37-8) + phenyl chloroformate (1885-14-9) → 6-chloro-2-phenoxycarbonyloxy-indole-1-carboxylic acid phenyl ester (301700-14-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Acylation;	92%
With triethylamine In tetrahydrofuran

6-chloro-2-oxindole (56341-37-8) → 6-chloroindoline-2-thione (392332-34-2)

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 (56341-37-8) + 2-chloropropionyl chloride (625-36-5) → 6-chloro-5-(3-chloro-propionyl)-1,3-dihydro-indol-2-one (860024-14-2)

Conditions	Yield
With aluminum (III) chloride In carbon disulfide at 20℃; for 3h; Heating / reflux;	92%

6-chloro-2-oxindole (56341-37-8) → 6-chloro-2-oxindole-3-thione S-oxide (1261171-12-3)

Conditions	Yield
With thionyl chloride In acetonitrile at 25 - 30℃; for 0.166667h;	92%

3-bromo-2-fluorobenzaldehyde (149947-15-9) + 6-chloro-2-oxindole (56341-37-8) → (E/Z)-3-(3-bromo-2-fluoro-benzylidene)-6-chloro-1,3-dihydro-indol-2-one (1309685-47-9)

Conditions	Yield
With piperidine In methanol at 80℃; for 2h;	92%

6-chloro-2-oxindole (56341-37-8) + 3-chloro-5-fluorobenzaldehyde (90390-49-1) → (3E/Z)-6-chloro-3-(3-chloro-5-fluorobenzylidene)-1,3-dihydro-2H-indol-2-one (1309685-27-5)

Conditions	Yield
With piperidine In methanol at 80℃; for 2h;	92%

6-chloro-2-oxindole (56341-37-8) + chloroacetyl chloride (79-04-9) → 6-chloro-5-(2-chloroacetyl) indolin-2-one (118307-04-3)

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 (56341-37-8) + 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (1160653-87-1) → E/Z-4-[4-bromo-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester (1162669-96-6)

Conditions	Yield
With piperidine In methanol at 100℃; for 3h;	90%

6-chloro-2-oxindole (56341-37-8) + p-Chlorothiophenol (106-54-7) → 6-chloro-3-((4-chlorophenyl)thio)indolin-2-one

Conditions	Yield
With iron(III) chloride; potassium carbonate In dimethyl sulfoxide at 50℃; for 1.5h; Green chemistry;	90%

6-chloro-2-oxindole (56341-37-8) + malononitrile (109-77-3) → 2-(6-chloro-2-oxoindolin-3-ylidene)malononitrile (1356828-86-8)

Conditions	Yield
With iron(III) chloride hexahydrate; oxygen In N,N-dimethyl-formamide at 50℃; for 5h; Green chemistry;	90%

6-chloro-2-oxindole (56341-37-8) → 6-chloroisatin (6341-92-0)

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

6-chloro-2-oxindole (56341-37-8) + azulene (275-51-4) → 1-(6-chloroindol-2-yl)azulene (1365097-46-6)

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 (56341-37-8) + 4-methyl-benzaldehyde (104-87-0) → (E)-3-(4-methylbenzylidene)-6-chloroindolin-2-one (1612883-15-4)

Conditions	Yield
With piperidine In ethanol for 3h; Reflux;	89%

6-chloro-2-oxindole (56341-37-8) + (3-oxo-butyl)-propyl-carbamic acid tert-butyl ester → 4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester

Conditions	Yield
With pyrrolidine In isopropyl alcohol at 90℃; for 48h;	88%

6-chloro-2-oxindole (56341-37-8) + 4-(Methylthio)benzaldehyde (3446-89-7) → (E)-3-(4-(methylthio)benzylidene)-6-chloroindolin-2-one (1612883-12-1)

Conditions	Yield
With piperidine In ethanol for 3h; Reflux;	88%

piperidine (110-89-4) + 1H-indol-2-ylcarboxaldehyde (19005-93-7) + 6-chloro-2-oxindole (56341-37-8) → 6-chloro-3-(1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one

Conditions	Yield
In ethanol	87%

6-chloro-2-oxindole (56341-37-8) + acetic anhydride (108-24-7) → 1-acetyl-6-chloroindolin-2-one (651747-72-7)

Conditions	Yield
at 130℃; for 7h;	87%
With sodium carbonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;

Upstream product

• 2564-05-8 2-chloro-N-(3-chlorophenyl)acetamide 
• 588-07-8 3-Chloroacetanilide 
• 623-48-3 ethyl iodoacetae 
• 37777-71-2 4-chloro-2-nitro-phenylacetic acid 
• 177985-31-8 (2-amino-4-chlorophenyl)acetic acid 
• 17122-55-3 Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide 
• 1261152-95-7 6-chloro-3-iminoindolin-2-one 
• 108-42-9 3-chloro-aniline 
• 6341-92-0 6-chloroisatin 
• 89-61-2 2,5-dichloronitrobenzene 
• 147124-32-1 dimethyl (4-chloro-2-nitrophenyl)malonate 
• 10565-16-9 (4-Chlor-2-nitro-phenyl)-malonsaeure-diaethylester 
• 879-32-3 6-chloroisatin 3-hydrazone 
• 147124-37-6 methyl 2-(4-chloro-2-nitrophenyl)acetate 

Downstream Products

• 83254-83-5 6-chloro-1-phenylindolin-2-one 
• 860798-05-6 (E)-3-benzylidene-6-chloro-1,3-dihydro-indol-2-one 
• 865079-99-8 (E)-6-chloro-3-(3-methoxy-benzylidene)-1,3-dihydro-indol-2-one 
• 860798-06-7 6-chloro-3-[1-(3-chloro-phenyl)-meth-(E)-ylidene]-1,3-dihydro-indol-2-one 
• 1148119-14-5 (E)-6-chloro-3-(3-hydroxy-4-methoxybenzylidene)indolin-2-one 
• 1148119-17-8 (E)-6-chloro-3-(3'-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one 
• 1001336-75-9 E/Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-methyl-propionic acid tert-butyl ester 
• 1443787-58-3 C₁₈H₁₆ClNO₄ 
• 1612882-99-1 (E)-3-(2-nitrobenzylidene)-6-chloroindolin-2-one 
• 1612883-00-7 (E)-3-(3-ethoxy-2-hydroxybenzylidene)-6-chloroindolin-2-one 
• 1612883-02-9 (E)-3-(4-hydroxybenzylidene)-6-chloroindolin-2-one 
• 1612883-03-0 (E)-3-(2,4-dichlorobenzylidene)-6-chloroindolin-2-one 
• 1612883-04-1 (E)-3-(2-hydroxy-3-methoxybenzylidene)-6-chloroindolin-2-one 
• 1612883-05-2 (E)-3-(4-nitrobenzylidene)-6-chloroindolin-2-one 

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The cyclic hydroxamic acid functional group is critical to the biological activity of numerous natural products and drug candidates. Efficient, reliable, and green synthetic methods to produce cyclic hydroxamic acids are needed. Herein, flow hydrogenation has been explored as a novel approach toward achieving the selective partial reduction of 2-nitrophenylacetic acid to 1-hydroxyindolin-2-one. The bidentate ligand, 1,10-phenanthroline, has been identified as a unique inhibitor for modulating product selectivity in this Pt/C-catalyzed process. Under the newly optimized reaction conditions, the targeted hydroxamic acid is produced with high selectivity (49:1) over the lactam by-product. The scope of the reaction is demonstrated for a variety of 2-nitrophenylacetic acid derivatives.

A Benzisoelenazolone modified pyrrole methyl ester substituted indole ketone compound and use thereof

The invention discloses a benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound and a use thereof. The invention depends on and claims the priority of a Chinese patent application 201110105248.0 submitted on April 26, 2011. Through reference, all contents of the Chinese patent application 201110105248.0 are incorporated into the invention. The benzisoselenazolone-modified pyrrolyl formate-substituted indolone compound is shown in the general formula I. The 2-indolone compound provided by the invention has excellent antitumor activity and can be widely used for preparation of antitumor drugs.

Palladium-Catalyzed C-H Activation and Cyclization of Anilides with 2-Iodoacetates and 2-Iodobenzoates: An Efficient Method toward Oxindoles and Phenanthridones

A concise approach to the synthesis of oxindoles and phenanthridones from anilides is described. In the presence of catalytic amount of Pd(OAc)2, 2-iodoacetates and 2-iodobenzoates can be used to functionalize ortho C-H bond of anilides, which subsequently undergo intramolecular cyclization to give the products. A possible reaction mechanism that involves a PdII/PdIV catalytic cycle is proposed with the support of detailed mechanistic studies.