15362-40-0

Basic information

• Product Name: 1-(2,6-Dichlorophenyl)indolin-2-one
• Synonyms: 1-(2,6-Dichlorophenyl)indolin-2-one;1-(2,6-dichlorophenyl)-1,3-dihydro-2h-indol-2-one;1-(2,6-Dichlorophenyl)-2-hydroxyindole;1,3-dihydro-1-(2,6-dichlorophenyl)-2h-indol-2-on;1,3-dihydro-1-(2,6-dichlorophenyl)-2h-indol-2-one;DICLOFENAC RELATED COMPOUND A (50 MG) (N-(2,6-DICHLOROPHENYL)INDOLIN-2-ONE);N-(2,6-Dichlorophenyl)-Indolin-(2)-One;hydroxyindole
• CAS NO: 15362-40-0
• Molecular Formula: C₁₄H₉Cl₂NO
• Molecular Weight: 278.13
• EINECS: 239-399-3
• Product Categories: Aromatics;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 15362-40-0.mol
• Article Data: 27

Chemical Properties

• Melting Point: 115-119°C
• Boiling Point: 488.6 ºC at 760 mmHg
• Flash Point: 249.3 ºC
• Appearance: /
• Density: 1.432 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -4.85±0.20(Predicted)
• Stability: Stability
• BRN: 1538309
• CAS DataBase Reference: 1-(2,6-Dichlorophenyl)indolin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-Dichlorophenyl)indolin-2-one(15362-40-0)
• EPA Substance Registry System: 1-(2,6-Dichlorophenyl)indolin-2-one(15362-40-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: NM3259200
• Hazardous Substances Data: 15362-40-0(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Light Brown Solid

Uses

1-(2,6-Dichlorophenyl)indolin-2-one is a potential prodrug of Diclofenac and possible impurity during its commercial synthesis. It is Aceclofenac EP Impurity I and Diclofenac Impurity A.

InChI:InChI=1/C14H9Cl2NO/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(17)18/h1-7H,8H2

Synthetic route

1-(2,6-dichlorophenyl)-3-(methylthio)oxindole (83281-94-1) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With zinc In acetic acid for 4h; Heating;	97%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;	94%
With thionyl chloride In dichloromethane; ethyl acetate at 50℃; for 2h; Concentration; Temperature;	92%
With hydrogenchloride In acetonitrile at 78.85℃; for 5h; Rate constant; Kinetics; Mechanism; energy data: ΔH(activ.), ΔS(activ.); ΔE(activ.)var. amount of acetonitrile, var. temp.;

2,2-dimethyl-1,3-dioxolane (2916-31-6) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 5-(2,6-dichloro-phenyl)-6,6-dimethyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions	Yield
With toluene-4-sulfonic acid In ethanol Cyclization;	A n/a B 93%

N-phenyl-2,6-dichloroaniline (15307-93-4) + chloroacetyl chloride (79-04-9) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
Stage #1: N-phenyl-2,6-dichloroaniline; chloroacetyl chloride at 100℃; for 3h; Stage #2: With aluminum (III) chloride at 100℃; for 1h; Temperature;	89%

2-ethyl-2-methyl-1,3-dioxolane (126-39-6) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 5-(2,6-dichloro-phenyl)-6-ethyl-6-methyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions	Yield
With toluene-4-sulfonic acid In ethanol Cyclization;	A n/a B 84%

diclofenac sodium (15307-79-6) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With sodium hydride; Phenoxyacetyl chloride In tetrahydrofuran for 18h; Inert atmosphere;	84%
Stage #1: diclofenac sodium With hydrogenchloride; water for 0.166667h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran for 3h;	47%
With sodium hydroxide In water at 123℃; for 0.5h; pH=8.41; Activation energy; Kinetics; Product distribution; Further Variations:; pH-values; Temperatures;	1.7%

2-chloro-N-(2,6-dichlorophenyl)acetamide (3644-56-2) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With aluminium trichloride 1.) 145-150 deg C, 2.) 162-168 deg C, 2 h;	81.3%

1-(2',6'-dichlorophenyl)-3-hydroxymethylene-2-indolinone → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With quinoline for 1h; Heating;	78%

2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide (15308-01-7) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With aluminium trichloride at 160℃; for 2h;	75.4%
With aluminum (III) chloride at 160℃; for 2h;	62%
With aluminum (III) chloride at 160℃; for 2h;
With triethylamine hydrochloride-aluminum trichloride at 20 - 60℃; for 4.5h; Reagent/catalyst;

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate (1528769-06-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	A 21% B 74%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + 2-phenyl-[1,3]dioxan-5-ol (1708-40-3) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 2-phenyl-1,3-dioxan-5-yl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate (1528769-07-4)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	A 30% B 68%

N-chloro-N-(2,6-dichlorophenyl)phenylacetamide → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Reagent/catalyst; Cooling with ice;	66.2%
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; Reagent/catalyst; Temperature; Friedel-Crafts Alkylation;	66.2%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + 2-phenyl-1,3-dioxan-5-yl 4-hydroxybenzoate (1402923-75-4) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 2-phenyl-1,3-dioxan-5-yl 4-(2-(2-((2,6-dichlorophenyl)amino)phenyl)acetoxy)benzoate (1528768-69-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	A 37% B 62%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + 2-{Methyl[(sulfanylcyclohexyl)methyl]amino}ethan-1-ol (306776-38-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 2-{Methyl[(sulfanylcyclohexyl)methyl]amino}ethyl-2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetate + [2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid 2-[(1-{2-[2-(2,6-dichloro-phenylamino)-phenyl]-acetylsulfanyl}-cyclohexylmethyl)-methyl-amino]-ethyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Acylation;	A n/a B 57% C n/a

2-[2-(2,6-dichlorophenyl)aminophenyl]acetyl chloride (65950-49-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + methyl iodide (74-88-4) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + (E)-1-(2,6-dichlorophenyl)-3-((methylselanyl)methylene)indolin-2-one

Conditions	Yield
Stage #1: 2-[2-(2,6-dichlorophenyl)aminophenyl]acetyl chloride; N,N-dimethyl-formamide With oxalyl dichloride; hydrogen selenide; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran; water at 25℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; water at 25℃; for 24h; Reagent/catalyst;	A 49% B 10%

2-methyl-2-phenyl-1,3-dioxolane (3674-77-9) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 5-(2,6-dichloro-phenyl)-6-methyl-6-phenyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions	Yield
With toluene-4-sulfonic acid In ethanol Cyclization;	A n/a B 47%

[2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + acetaldehyde (75-07-0) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 5-(2,6-dichloro-phenyl)-6-methyl-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions	Yield
With toluene-4-sulfonic acid In ethanol Cyclization;	A n/a B 33%

formaldehyd (50-00-0) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 5-(2,6-dichloro-phenyl)-5,9-dihydro-6H-7-oxa-5-aza-benzocyclohepten-8-one

Conditions	Yield
With toluene-4-sulfonic acid In ethanol Cyclization;	A n/a B 25%

methanol (67-56-1) + diclofenac sodium (15307-79-6) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 2-((2,6-dichlorophenyl)amino)benzaldehyde (22121-58-0) + 2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester (15307-78-5)

Conditions	Yield
With water at 19.85℃; for 17532h; Kinetics; Product distribution; Further Variations:; rel. humidity; complexed with β-cyclodextrin; Decarboxylation; oxidation, cyclization, esterification;

diclofenac sodium (15307-79-6) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 1-(2,6-Dichlorphenyl)-2,3-indoldion (24542-74-3) + 2-[(2,6-dichlorophenyl)amino]benzyl alcohol (27204-57-5) + 4-chloro-10H-9-acridinone

Conditions	Yield
at 79.85℃; for 17532h; Kinetics; Activation energy; Thermodynamic data; Further Variations:; Temperatures; Decomposition;

diclofenac sodium - β-cyclodextrin inclusion complex → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 1-(2,6-Dichlorphenyl)-2,3-indoldion (24542-74-3) + 2-[(2,6-dichlorophenyl)amino]benzyl alcohol (27204-57-5) + 4-chloro-10H-9-acridinone

Conditions	Yield
at 79.85℃; for 17532h; Kinetics; Activation energy; Thermodynamic data; Further Variations:; Temperatures; Decomposition;

methanol (67-56-1) + diclofenac sodium (15307-79-6) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester (15307-78-5) + 1-(2,6-Dichlorphenyl)-2,3-indoldion (24542-74-3)

Conditions	Yield
Stage #1: diclofenac sodium With β‐cyclodextrin complexation; Stage #2: With water at 19.85℃; for 17532h; Cyclization; oxidation; Stage #3: methanol Esterification;

diclofenac sodium (15307-79-6) → 2-oxoindole (59-48-3) + 2,6-Dichlorophenol (87-65-0) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5)

Conditions	Yield
In phosphate buffer at 45℃; Kinetics; Thermodynamic data; Further Variations:; pH-values; Temperatures;

1-(2',6'-dichlorophenyl)-3-dimethylaminomethylene-2-indolinone (175983-50-3) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85.5 percent / NaOH / propan-2-ol; H2O / 6.5 h / Heating 2: 78 percent / quinoline / 1 h / Heating View Scheme

N-phenyl-2,6-dichloroaniline (15307-93-4) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: benzene / 6 h / Heating 2: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 3: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 4: 97 percent / Zn / acetic acid / 4 h / Heating View Scheme
Multi-step reaction with 4 steps 1: benzene / 6 h / Heating 2: N-chlorosuccinimide / CCl4 / 1 h / Ambient temperature 3: SnCl4 / CCl4 / 0.83 h / Ambient temperature 4: 97 percent / Zn / acetic acid / 4 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 66 percent / 16 h / Heating 2: 75.4 percent / AlCl3 / 2 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: 5 h / Reflux 2: aluminum (III) chloride / 2 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: toluene / 3 h / 120 °C 2: triethylamine hydrochloride-aluminum trichloride / 4.5 h / 20 - 60 °C View Scheme

N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide (83281-93-0) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / Ambient temperature 2: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 3: 97 percent / Zn / acetic acid / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: N-chlorosuccinimide / CCl4 / 1 h / Ambient temperature 2: SnCl4 / CCl4 / 0.83 h / Ambient temperature 3: 97 percent / Zn / acetic acid / 4 h / Heating View Scheme

N-(2,6-dichlorophenyl)-α-(methylsulfinyl)acetanilide (83281-96-3) → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 2: 97 percent / Zn / acetic acid / 4 h / Heating View Scheme

α-chloro-N-(2,6-dichlorophenyl)-α-(methylthio)acetanilide → 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: SnCl4 / CCl4 / 0.83 h / Ambient temperature 2: 97 percent / Zn / acetic acid / 4 h / Heating View Scheme

diclofenac sodium (15307-79-6) → 2-oxoindole (59-48-3) + 2,6-Dichlorophenol (87-65-0) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 4-chloro-10(H)acridin-9-one (69220-40-2) + 2,6-dichloronitrobenzene (601-88-7) + N-phenyl-2,6-dichloroaniline (15307-93-4) + N-(2,6-dichlorophenyl)-formamide (10113-35-6) + 1,3-dichloro-2-isocyanobenzene (6697-95-6) + 2,6-dichlorophenylisocyanate (39920-37-1) + 4-chloro-1,3-benzoxazol-2(3H)-one (13603-93-5) + 2,6-Dichloroaniline (608-31-1)

Conditions	Yield
With dihydrogen peroxide; iron(II) In water at 20℃; pH=2; Fenton Reaction;

...Expand

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + acetone (67-64-1) → 1-(2,6-Dichlorophenyl)-3-isopropylidene-1,3-di-hydro-2H-indol-2-one (869741-84-4)

Conditions	Yield
With pyrrolidine for 3h; Heating / reflux;	97%

(E)-3-phenylpropenal (14371-10-9) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → (3Z)-1-(2,6-dichlorophenyl)-3-((E)-3-phenylallylidene)indolin-2-one (1257095-18-3)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Neat (no solvent); Microwave irradiation;	95%

Indole-3-carboxaldehyde (487-89-8) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → (Z)-3-((1H-indol-3-yl)methylene)-1-(2,6-dichlorophenyl)indolin-2-one (1257094-96-4)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Microwave irradiation; Neat (no solvent);	95%

2,3,4,5-tetrahydro-6-methoxypyridine (5693-62-9) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → 1-(2,6-dichlorophenyl)-3-(piperidin-2-ylidene)indolin-2-one

Conditions	Yield
for 1.75h; Condensation; Heating;	93.8%

O-methylcaprolactim (2525-16-8) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → 1-(2,6-dichlorophenyl)-3-(hexahydroazepin-2-ylidene)indolin-2-one

Conditions	Yield
for 1h; Condensation; Heating;	93.2%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → diclofenac sodium (15307-79-6)

Conditions	Yield
With sodium hydroxide In ethanol; water for 4h; Heating;	93%
With sodium dithionite; water; sodium hydroxide for 6h; Reflux;	92.3%
With sodium hydroxide In ethanol for 3h; Heating;	85%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In toluene for 10h; Reflux;	83.6%
With sodium hydroxide for 2h; Temperature; Reflux;	4.035 g

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 4-picolylchloride hydrochloride (1822-51-1) → N-(2,6-dichlorophenyl)-3,3-di(4-pyridylmethyl)-2-indolinone

Conditions	Yield
With potassium fluoride on basic alumina for 0.0833333h; microwave irradiation;	92%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + C18H15NO (1257094-79-3) → (3Z)-1-(2,6-dichlorophenyl)-3-((1-cinnamyl-1H-indol-3-yl)methylene)indolin-2-one (1257095-04-7)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Microwave irradiation; Neat (no solvent);	91%

3-formyl-6-isopropylchromone (49619-58-1) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → 1-(2,6-dichlorophenyl)-3-(6-isopropyl-4-oxo-4H-chromen-3-ylmethylene)-1,3-dihydro-indol-2-one (1598426-36-8)

Conditions	Yield
for 0.0166667h; Microwave irradiation;	91%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + zinc(II) hydroxide → zinc diclofenac

Conditions	Yield
With hydrogenchloride; potassium hydroxide In water at 85℃; for 8h;	91%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 1-benzoyl-1H-indole-3-carbaldehyde (27092-42-8) → C30H18Cl2N2O2

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Microwave irradiation; Neat (no solvent);	90%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + zinc(II) sulfate (7733-02-0) → zinc diclofenac

Conditions	Yield
Stage #1: 1-(2,6-dichlorophenyl)indolin-2-one With potassium hydroxide In water at 100℃; for 5h; Stage #2: zinc(II) sulfate In water at 85℃; for 1h;	90%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + N,N-dimethylformamide diethyl diacetal (1188-33-6) → 1-(2',6'-dichlorophenyl)-3-dimethylaminomethylene-2-indolinone (175983-50-3)

Conditions	Yield
In isopropyl alcohol at 20℃; for 22h;	89%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 9-anthracene aldehyde (642-31-9) → (Z)-3-((anthracen-10-yl)methylene)-1-(2,6-dichlorophenyl)indolin-2-one (1257095-21-8)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Neat (no solvent); Microwave irradiation;	89%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + zinc(II) chloride (7646-85-7) → zinc diclofenac

Conditions	Yield
Stage #1: 1-(2,6-dichlorophenyl)indolin-2-one With potassium hydroxide In water at 100℃; for 5h; Stage #2: zinc(II) chloride In water at 85℃; for 1h;	89%

2-pyrrole aldehyde (1003-29-8) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → (Z)-3-((1H-pyrrol-2-yl)methylene)-1-(2,6-dichlorophenyl)indolin-2-one

Conditions	Yield
With piperidine In chloroform at 100℃; for 1h; Microwave irradiation;	87.2%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 3-Formylchromone (17422-74-1) → 1-(2,6-dichlorophenyl)-3-(4-oxo-4H-chromen-3-ylmethylene)-1,3-dihydroindol-2-one (1598426-34-6)

Conditions	Yield
for 0.0166667h; Microwave irradiation;	87%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 6-bromo-4-oxo-4H-chromene-3-carbaldehyde (52817-12-6) → 3-(6-bromo-4-oxo-4H-chromen-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one (1598426-35-7)

Conditions	Yield
for 0.0166667h; Microwave irradiation;	87%

pyridine-2-carbaldehyde (1121-60-4) + 1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → (Z)-1-(2,6-dichlorophenyl)-3-((pyridin-2-yl)-methylene)indolin-2-one (1257095-19-4)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Neat (no solvent); Microwave irradiation;	86%
for 0.0166667h; Microwave irradiation;	86%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + indole-2,3-dione (91-56-5) → (E)-1-(2,6-dichlorophenyl)-[3,3'-biindolinylidene]-2,2'-dione

Conditions	Yield
With zirconium(IV) chloride In ethanol for 12h; Reflux;	86%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 1-(prop-2-yn-1-yl)-1H-indole-3-carbaldehyde → (Z)-1-(2,6-dichlorophenyl)-3-((1-(prop-2-ynyl)-1H-indol-3-yl)methylene)indolin-2-one (1257094-98-6)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Microwave irradiation; Neat (no solvent);	85%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) → [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5)

Conditions	Yield
In hydrogenchloride; toluene liquid HCl;	84.4%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 2-Trifluoromethylbenzaldehyde (447-61-0) → 1-(2,6-dichlorophenyl)-3-(2-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one (1574402-28-0)

Conditions	Yield
Microwave irradiation;	84%

1-(2,6-dichlorophenyl)indolin-2-one (15362-40-0) + 4-nitrobenzaldehdye (555-16-8) → (Z)-3-(4-nitrobenzylidene)-1-(2,6-dichlorophenyl)indolin-2-one (1257095-20-7)

Conditions	Yield
With sodium hydrogencarbonate Knoevenagel condensation; Neat (no solvent); Microwave irradiation;	83%

Upstream product

• 3644-56-2 2-chloro-N-(2,6-dichlorophenyl)acetamide 
• 15308-01-7 2-chloro-N-(2',6'-dichlorophenyl)-N-phenylacetamide 
• 83281-94-1 1-(2,6-dichlorophenyl)-3-(methylthio)oxindole 
• 2916-31-6 2,2-dimethyl-1,3-dioxolane 
• 15307-86-5 [2-(2,6-dichloroanilino)phenyl]acetic acid 
• 126-39-6 2-ethyl-2-methyl-1,3-dioxolane 
• 50-00-0 formaldehyd 
• 3674-77-9 2-methyl-2-phenyl-1,3-dioxolane 
• 75-07-0 acetaldehyde 
• 67-56-1 methanol 
• 15307-79-6 diclofenac sodium 
• 587-65-5 N-chloroacetyl-aniline 
• 65950-49-4 2-[2-(2,6-dichlorophenyl)aminophenyl]acetyl chloride 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 869741-86-6 (E)-1-(2,6-dichlorophenyl)-3-(4-methyl-benzylidene)-1,3-dihydro-2H-indol-2-one 
• 869741-84-4 1-(2,6-Dichlorophenyl)-3-isopropylidene-1,3-di-hydro-2H-indol-2-one 
• 1529772-93-7 1-(2,6-dichlorophenyl)-3-{1-[3-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)propyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one 
• 1529772-94-8 1-(2,6-dichlorophenyl)-3-{1-[4-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)butyl]-1H-indol-3-ylmethylene}-1,3-dihydro-indol-2-one 
• 1574402-12-2 3-(5-bromo-1H-indol-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one 
• 1574402-13-3 1-(2,6-dichlorophenyl)-3-(5-methoxy-1H-indol-3-ylmethylene)-1,3-dihydroindol-2-one 
• 1574402-19-9 3-(1-benzyl-5-bromo-1H-indol-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydro-indol-2-one 
• 1574402-20-2 3-[5-bromo-1-(4-chlorobenzoyl)-1H-indol-3-ylmethylene]-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one 
• 1574402-21-3 3-[5-bromo-1-(2-fluorobenzyl)-1H-indol-3-ylmethylene]-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one 
• 1574402-26-8 3-(1-benzyl-5-methoxy-1H-indol-3-ylmethylene)-1-(2,6-dichlorophenyl)-1,3-dihydroindol-2-one 
• 1574402-28-0 1-(2,6-dichlorophenyl)-3-(2-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one 

Related news

Densitometric determination of diclofenac, 1-(2,6-dichlorophenyl)indolin-2-one and indolin-2-one in pharmaceutical preparations and model solutions08/07/2019

A chromatographic-densitometric method for identification and quantitation of diclofenac and its impurities, i.e. 1-(2,6-dichlorophenyl)indolin-2-one and indolin-2-one in pharmaceutical preparations and model solutions was developed. The effect of pH, temperature and ultra violet (UV) radiation ...detailed

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Vilsmeier reagent, NaHSe and diclofenac acid chloride: One-pot synthesis of a novel selenoindolinone with potent anticancer activity

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The invention discloses a synthesis method of diclofenac sodium, which comprises the following steps: (1) toluene. An oil layer is obtained by adding 2, 6 -dichlorophenol and sodium carbonate, keeping warm and refluxing, extracting the oil layer with water, and adding an alkali heat-preserving reaction in the oil layer to obtain 2, 6 -dichloroaniline. (2) 1, 2 Dichlorodimethylaniline prepared in step (6 -) is heated and melted, chloroacetyl chloride is added dropwise, and the heat is subjected to heat preservation reaction after being heated to crystallize to obtain N - (2, 6 - dichlorophenyl) - phenyl - chloroacetamide. (3) 2 (N - 2 Dichlorophenyl) 6 - phenyl - chloroacetamide prepared in step (-) is reacted with the aluminum trichloride to give a solid 1 - (2, 6 -dichlorophenyl) -2 -indolinone. (4) 3 (1 - 2-dichlorophenyl) 6 -indolinone prepared in step (-2 -) is added to alkali liquor, stirred and heated to reflux to obtain diclofenac sodium. The synthesis method is stable, easy to operate, low in cost, high in yield and suitable for industrial production.

Preparation method of 2-[(2, 6-dichlorophenyl) amino] sodium phenylacetate

The invention belongs to the field of chemical pharmacy, and relates to a production process of a chemical bulk drug, in particular to a preparation method of 2-[(2, 6-dichlorophenyl) amino] sodium phenylacetate. The preparation method comprises the following steps: taking 2, 6-dichlorodiphenylamine and chloroacetyl chloride as initial raw materials; and completing acylation reaction, Lewis acidicionic liquid catalyzed Friedel-Crafts alkylation reaction and hydrolysis reaction by a one-pot method to finally obtain the 2-[(2, 6-dichlorophenyl) amino] sodium phenylacetate. The 2-[(2,6-dichlorophenyl) amino] sodium phenylacetate is synthesized by adopting a one-pot preparation scheme, has the advantages of short reaction time, simplicity in operation, mild conditions, high yield, good catalytic effect, high selectivity, recyclability and the like, and is beneficial to industrial production.