5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol | 100% |
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 20℃; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid at 20 - 30℃; for 1.66667h; | 97.3% |
Stage #1: 2-hydroxyimino-N-p-tolyl-acetamide With sulfuric acid at 60 - 80℃; Stage #2: With water for 0.5h; Cooling with ice; | 86.9% |
Stage #1: 2-hydroxyimino-N-p-tolyl-acetamide With sulfuric acid at 20℃; Sandmeyer reaction; Stage #2: With water Cooling with ice; | 85% |
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 5h; | 92.7% |
Conditions | Yield |
---|---|
With oxygen; sodium iodide In tetrahydrofuran at 60℃; for 12h; Schlenk technique; chemoselective reaction; | 92% |
Multi-step reaction with 2 steps 1: CuBr2 / ethyl acetate / 80 °C 2: water / methanol / 2 h / Heating View Scheme | |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 18h; |
5-methyl-2,3-dihydro-1H-indole
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With iodine pentoxide In dimethyl sulfoxide at 80℃; | 88% |
With o-iodosobenzoic acid; oxygen In dimethyl sulfoxide at 80℃; for 12h; Green chemistry; | 83% |
(Z)-2-(hydroxylimino)-N-p-tolylacetamide
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With sulfuric acid at 50 - 80℃; | 86.9% |
Conditions | Yield |
---|---|
With oxygen; Rose Bengal lactone In water; N,N-dimethyl-formamide for 18h; Inert atmosphere; Irradiation; | 86% |
With N-iodo-succinimide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 15 - 25℃; for 4h; | 83% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; oxygen In acetonitrile at 20℃; for 11h; | 82% |
With tert.-butylhydroperoxide; iodine In dimethyl sulfoxide at 80℃; for 24h; | 64% |
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With copper(I) bromide In water; benzonitrile at 140℃; for 4h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
Stage #1: chloral hydrate; p-toluidine With sulfuric acid; hydroxylamine hydrochloride; sodium sulfate In water at 130℃; for 0.5h; Stage #2: With sulfuric acid at 50 - 70℃; for 1h; | 80% |
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water at 90℃; for 0.0833333h; | 66.3% |
Stage #1: chloral hydrate; p-toluidine With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water Stage #2: With sulfuric acid at 60 - 80℃; | 56% |
5-methylindole-3-carboxaldehyde
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With sodium chloride In water; acetonitrile at 50℃; for 2h; Green chemistry; | 80% |
Conditions | Yield |
---|---|
With H-β zeolite In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; | 76% |
carbon monoxide
N'-(2-Bromo-4-methylphenyl)-N,N-dimethylurea
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
Stage #1: N'-(2-Bromo-4-methylphenyl)-N,N-dimethylurea With methyllithium In tetrahydrofuran; diethyl ether at 0℃; Stage #2: With tert.-butyl lithium In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 1h; Stage #3: carbon monoxide In tetrahydrofuran; diethyl ether; n-heptane at 0℃; for 0.5h; | 72% |
Yield given; Multistep reaction; |
3-(p-tolylimino)-5-methyl-N-p-tolyl-3H-indole-2-amine
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In water for 0.333333h; Reflux; | 68% |
5-methylisatin-3-oxime
triisopropyl phosphite
A
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 12h; | A n/a B n/a C 60% |
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 12h; | A n/a B n/a C 60% |
Conditions | Yield |
---|---|
With copper(II) choride dihydrate; caesium carbonate; trifluoroacetic acid In 2-methyltetrahydrofuran; water at 70℃; for 5h; Schlenk technique; Inert atmosphere; | 47% |
Conditions | Yield |
---|---|
With nitrobenzene Erwaermen des Reaktionsgemisches mit Aluminiumchlorid; |
Conditions | Yield |
---|---|
With acetone Man oxydiert das (nicht isolierte) <6-Nitro-α-oxy-3-methyl-benzyl>-aceton mit Kaliumpermanganat in sodaalkalischer Loesung bei 60-70grad; |
2-hydroxyimino-N-p-tolyl-acetamide
A
5-methyl-indole-2,3-dione
B
p-tolyl-oxalamide
Conditions | Yield |
---|---|
With PPA |
Conditions | Yield |
---|---|
With sulfuric acid | |
With sulfuric acid |
di-p-toluidino-acetic acid ethyl ester
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With mineral acid |
5-methylisatin-3-oxime
phosphorous acid trimethyl ester
A
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 12h; |
5-methylisatin-3-oxime
phosphorous acid trimethyl ester
A
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With acetic acid at 100℃; for 12h; |
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With sulfuric acid Darstellung; |
sulfuric acid
5-methyl-1-tosylindoline-2,3-dione
5-methyl-indole-2,3-dione
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With hydrogenchloride | |
With hydrogenchloride |
5-methyl-indole-2,3-dione
7-bromo-5-methyl-2,3-dihydro-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 20℃; for 24h; | 100% |
With water; bromine | |
With chloroform; bromine | |
With bromine In acetic acid |
5-methyl-indole-2,3-dione
2-oxo-propionic acid
6-methylquinoline-2,4-dicarboxylic acid
Conditions | Yield |
---|---|
Stage #1: 5-methyl-indole-2,3-dione; 2-oxo-propionic acid With potassium hydroxide In water at 40℃; for 12h; Stage #2: With hydrogenchloride In water pH=3; | 100% |
With potassium hydroxide In water at 40℃; for 12h; | 100% |
With potassium hydroxide In water at 40℃; for 16h; Pfitzinger Quinoline Synthesis; | 96% |
5-methyl-indole-2,3-dione
1-isopropyl-5-methylindoline-2,3-dione
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
5-methyl-indole-2,3-dione
5-methyl-1-propylindoline-2,3-dione
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
5-methyl-indole-2,3-dione
1-ethyl-5-methyl-2,3-indolinedione
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
5-methyl-indole-2,3-dione
1,5-dimethyl-1H-indole-2,3-dione
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; | 100% |
5-methyl-indole-2,3-dione
N-(2-bromophenyl)hydrazinecarbothioamide
5-methyl-1H-indole-2,3-dione 3-[N-(2-bromophenyl)thiosemicarbazone]
Conditions | Yield |
---|---|
With sulfuric acid In ethanol for 5h; Reflux; | 99% |
5-methyl-indole-2,3-dione
1-bromo-hexane
1-hexyl-5-methylindoline-2,3-dione
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 140℃; Microwave irradiation; | 99% |
5-methyl-indole-2,3-dione
nitromethane
3-hydroxy-5-methyl-3-(nitromethyl)-2,3-dihydro-1H-indol-2-one
Conditions | Yield |
---|---|
With (3ξ,8α,9R)-cinchonan-6',9-diol; benzoic acid In N,N-dimethyl acetamide at -15℃; for 3h; Henry reaction; optical yield given as %ee; enantioselective reaction; | 99% |
With 9-O-benzyl-6'-hydroxycinchonidine In tetrahydrofuran at -30℃; for 120h; Henry reaction; optical yield given as %ee; enantioselective reaction; | 92% |
In tetrahydrofuran at -10℃; for 11h; Henry reaction; optical yield given as %ee; enantioselective reaction; | 88% |
5-methyl-indole-2,3-dione
aminomalonic acid diethyl ester
dimethyl acetylenedicarboxylate
5',5'-diethyl 3',4'-dimethyl 5-methyl-2-oxospiro[indoline-3,2'-pyrrole]-3',4',5',5'(1'H)-tetracarboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; for 36h; Time; Molecular sieve; | 99% |
5-methyl-indole-2,3-dione
3-amino-1-phenyl-2-pyrazolin-5-one
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
Conditions | Yield |
---|---|
With acetic acid In water at 90℃; for 7h; Green chemistry; | 99% |
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With methanol; triethylamine at 20℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 80℃; for 16h; Kabachnik-Fields Reaction; Green chemistry; | 98% |
With magnetic nanoparticle γ-Fe2O3-immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene In neat (no solvent) at 60℃; for 5h; | 91% |
at 100℃; for 6h; | 80% |
With β‐cyclodextrin In methanol; water at 20℃; |
Conditions | Yield |
---|---|
With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 80℃; for 16h; Kabachnik-Fields Reaction; Green chemistry; | 98% |
With zinc(II) oxide In neat (no solvent) at 20℃; for 0.666667h; | 94% |
With magnetic nanoparticle γ-Fe2O3-immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene In neat (no solvent) at 60℃; for 6h; | 91% |
at 100℃; for 6h; | 80% |
With β‐cyclodextrin In methanol; water at 20℃; |
Conditions | Yield |
---|---|
In water at 20℃; for 4h; | 98% |
In ethanol Heating; | 72% |
With acetic acid In ethanol for 0.75h; Reflux; | |
With acetic acid at 20℃; for 2h; | |
In ethanol for 2h; Reflux; |
Conditions | Yield |
---|---|
With 60 wtpercent phosphotungstic acid supported on MCM-41 In tetrahydrofuran at 20℃; for 2.5h; Friedel-Crafts Acylation; | 98% |
With 1‐(2‐hydroxyethyl)‐1,4‐diazabicyclo[2.2.2]octanylium tetrachloroferrate In ethanol at 50℃; for 0.0833333h; Green chemistry; | 98% |
With boron trifluoride supported on nano-SiO2 In methanol for 0.45h; Reflux; | 95% |
2-{[5-(4-methoxyphenyl)-1,3,5-oxadiazol-2-yl]imino}-4-thiazolidinone
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With sodium acetate; acetic anhydride In acetic acid at 150 - 160℃; for 5h; | 98% |
2-Amino-6-((E)-nonadec-10-enyl)-benzoic acid
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
for 0.0666667h; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetic acid at 20 - 60℃; for 0.75h; | 98% |
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 16h; | 62% |
With boron trifluoride diethyl etherate; acetic acid at 60℃; |
5-methyl-indole-2,3-dione
2-Hydroxy-1,4-naphthoquinone
malononitrile
2-amino-5'-methyl-2',5,10-trioxo-5,10-dihydrospiro[benzo[g]chromene-4,3'-indoline]-3-carbonitrile
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In water for 3h; Reflux; | 98% |
With graphene oxide-supported dicationic ionic liquid In water for 0.333333h; Reflux; Green chemistry; | 95% |
5-methyl-indole-2,3-dione
edaravone
malononitrile
6'-amino-3',5'-dimethyl-2-oxo-1'-phenyl-1'H-spiro[indoline-3,4'-pyrano[2,3-c]pyrazole]-5'-carbonitrile
Conditions | Yield |
---|---|
With sodium chloride In water at 20℃; for 0.166667h; Sonication; | 98% |
With ammonium cerium (IV) nitrate In water at 20℃; for 0.166667h; Sonication; Green chemistry; | 98% |
With ZnS nanoparticles In water at 20℃; for 0.2h; ultrasonic irradiation; | 97% |
In water at 60℃; for 1h; | 92% |
With silica immobilized propyl imidazolium chloride In water for 0.5h; Reflux; | 88% |
5-methyl-indole-2,3-dione
4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one
2-mercaptopropanoic acid
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide In water Sonication; Combinatorial reaction / High throughput screening (HTS); | 98% |
5-methyl-indole-2,3-dione
2-methyl-3-bromo-1-propene
3-(2-methylallyl)-3-hydroxy-5-methyl-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With indium In decaethylene glycol at 20℃; for 0.25h; Barbier reaction; | 98% |
5-methyl-indole-2,3-dione
allyl bromide
3-allyl-3-hydroxy-5-methyl-1,3-dihydro-2H-indol-2-one
Conditions | Yield |
---|---|
With indium In decaethylene glycol at 20℃; for 0.166667h; Barbier reaction; | 98% |
1,3-benzothiazol-6-amine
5-methyl-indole-2,3-dione
3-(benzothiazol-6-ylimino)-1,3-dihydro-5-methyl-2H-indole-2-one
Conditions | Yield |
---|---|
In water at 20℃; for 3h; | 98% |
5-methyl-indole-2,3-dione
Conditions | Yield |
---|---|
With 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1S,2S)-2-(dimethylamino)cyclohexyl]thiourea In acetonitrile at 25℃; for 24h; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
Stage #1: ethyl acetoacetate With hydrazine hydrate for 0.0833333h; Stage #2: 5-methyl-indole-2,3-dione With sodium hydrogencarbonate In ethanol at 78℃; for 18h; | 98% |
Conditions | Yield |
---|---|
With acetic acid In water at 90℃; for 7h; Green chemistry; | 98% |
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