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CAS No.: | 608-05-9 |
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Name: | 5-Methylisatin |
Article Data: | 113 |
Molecular Structure: | |
Formula: | C9H7NO2 |
Molecular Weight: | 161.16 |
Synonyms: | Indole-2,3-dione,5-methyl- (7CI,8CI);Isatin, 5-methyl- (6CI);5-Methyl-1H-indole-2,3-dione;5-Methyl-2,3-indolinedione;5-Methylindole-2,3-dione;NSC 9398; |
EINECS: | 210-152-1 |
Density: | 1.301 g/cm3 |
Melting Point: | 180 °C (dec.)(lit.) |
Appearance: | orange crystalline |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 22-24/25-36-26 |
PSA: | 46.17000 |
LogP: | 1.26780 |
5-methyl-indole-2,3-dione
Conditions | Yield |
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With hydrogenchloride In ethanol | 100% |
5-methyl-indole-2,3-dione
Conditions | Yield |
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With hydrogenchloride In tetrahydrofuran; water at 20℃; | 99% |
Conditions | Yield |
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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 |
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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 |
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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% |