Structure of 453562-68-0
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CAS No. : | 453562-68-0 |
Formula : | C12H14N2O3 |
M.W : | 234.25 |
SMILES Code : | CC(N1CC(C)(C)C2=C1C=C([N+]([O-])=O)C=C2)=O |
MDL No. : | MFCD07636645 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319 |
Precautionary Statements: | P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogen;5% Pd(II)/C(eggshell); In tetrahydrofuran; at 60℃; under 1551.49 Torr; for 6h; | Example 6; Preparation of 1-(6-amino-3,3-dimethyl-indolin-1-1y)ethanone; [0073](1 eq.) (3 eq.) (5 wt%) (1 eq.)[0074] l-(3, 3-Dimethyl-6-nitroindoline-ly)ethanone (Example 5, 50 g), 5% Pd/C (1 g, 50% wet) and THF (200 mL) were charged to a 400 mL hydrogenation reactor. The slurry was degassed with vacuum/hydrogen three times and stirred for 6 h at 60 0C under hydrogen (30 PSI). The resulting mixture was filtered through a thin layer of Celite and the cake was washed with THF (150 mL x 2). The filtrate and washes were combined and concentrated in vacuo, followed by addition of toluene (150 mL). The product was isolated by filtration and the wet cake was washed with D.I. water (100 mL x 2) and 50 mL toluene to afford l-(6-amino-3, 3-dimethyl-indolin-l-yl)ethanone (38.5 g, 94% yield, >99.9 A%, 100 wt%). |
61% | Pd-C; In methanol; | DC-8; 1-(6-Amino-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone 10% Pd-C (0.2 g) was added to a suspension of 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone (2.1 g, 9 mmol) in MeOH (20 mL). The reaction was stirred under H2 (40 psi) at room temperature overnight. Pd-C was filtered off and the filtrate was concentrated under vacuum to give a crude product, which was purified by column chromatography to yield 1-(6-amino-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (DC-8) (1.3 g, 61%). |
61% | With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2068.65 Torr; | 10% Pd-C (0.2 g) was added to a suspension of 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone (2.1 g, 9 mmol) in MeOH (20 mL). The reaction was stirred under H2 (40 psi) at room temperature overnight. Pd-C was filtered off and the filtrate was concentrated under vacuum to give a crude product, which was purified by column chromatography to yield 1-(6-amino-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone (DC-8) (1.3 g, 61%). |
With hydrogen;palladium 10% on activated carbon; In methanol; | l-(3,3-Dimeth.Yl-6-nitro-2,3-dihydro-indol-l-Yl)ethanone (250mg) was dissolved in MeOH (20 mL), the mixture was bubbledwith H2 for 10 min. 10% Pd/C (50 mg) was added and themixture was stirred under H2 overnight. The mixture wasfiltered through Celite and concentrated in vacuo. Thecrude material was purified by flash chromatography onsilica gel with 1:1 EtOAc:CH2Cl2 to afford the titlecompound as a white crystalline material. MS: 205 (M+l).Calc'd. for Ci2H16N20-204 .27 . | |
With H2; In methanol; ethyl acetate; | EXAMPLE 133 Step A-Preparation of 1-acetyl-6-amino-3,3-dimethylindoline 1-Acetyl-3,3-dimethyl-6-nitroindoline (250 mg) was dissolved in MeOH (20 mL), the mixture was bubbled with H2 for 10 min. 10% Pd/C (50 mg) was added and the mixture was stirred under H2 overnight. The mixture was filtered through Celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1:1 EtOAc:CH2Cl2 to afford the title compound as a white crystalline material. MS: 205 (M+1). Calc'd. for C12H16N2O-204.27. | |
With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 3h; | C. 1-(6-amino-3,3-dimethylindolin-1-yl)ethanone A mixture of 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone (300 mg), 10% Pd-C (50 mg), and EtOH (50 mL) was stirred under hydrogen atmosphere (1 atm) for 3 h. The catalyst was filtered out and the filtrate was concentrated to give a light yellow solid (260 mg). MS: M+H=205. | |
Pd-C; In ethanol; | C. 1-(6-Amino-3,3-dimethylindolin-1-yl)ethanone A mixture of 1-(3,3-dimethyl-6-nitroindolin-1-yl)ethanone (300 mg, 1.3 mmol), 10% Pd-C (50 mg), and EtOH (50 mL) was stirred under H2 (1 atm) for 3 h. After that the catalyst was filtered off and the filtrate was concentrated to give a light yellow solid (260 mg). MS: M+H=205 (M+1); | |
With H2; In methanol; ethyl acetate; | Step A-Preparation of 1-acetyl-6-amino-3,3-dimethylindoline 1-Acetyl-3,3-dimethyl-6-nitroindoline (250 mg) was dissolved in MeOH (20 mL), the mixture was bubbled with H2 for 10 min. 10% Pd/C (50 mg) was added and the mixture was stirred under H2 overnight. The mixture was filtered through Celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1:1 EtOAc:CH2Cl2 to afford the title compound as a white crystalline material. MS: 205 (M+1). Calc'd. for C12H16N2O-204.27. | |
With hydrogen;palladium 10% on activated carbon; In ethanol; at 25℃; under 2250.23 Torr; for 1.16667h; | Stage f: 1-acetyl-3,3-dimethylindolin-6-amine 1.46 g of 10% palladium on charcoal, 8.8 g of 1-acetyl-3,3-dimethyl-6-nitroindoline obtained in stage e) below and 110 mL of ethanol are placed in a hydrogenation reactor. After reacting for one hour 10 minutes at 3 bar at a temperature of 25 C., the reaction medium is filtered through paper and concentrated under reduced pressure to give 6.9 g of 1-acetyl-3,3-dimethylindolin-6-amine in the form of a brown solid, the characteristics of which are as follows: LCMS: RT=1.12 min; m/z=205 [M+H]+ | |
With hydrogen;palladium 10% on activated carbon; In methanol; | Step A-Preparation of 1-acetyl-6-amino-3,3-dimethylindoline 1-Acetyl-3,3-dimethyl-6-nitroindoline (250 mg) was dissolved in MeOH (20 mL), the mixture was bubbled with H2 for 10 min. 10% Pd/C (50 mg) was added and the mixture was stirred under H2 overnight.The mixture was filtered through Celite and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 1:1 EtOAc:CH2Cl2 to afford the title compound as a white crystalline material. MS: 205 (M+1). Calc'd. for C12H16N2O-204.27. | |
With hydrogen;palladium 10% on activated carbon; In methanol; | Preparation LXXIX: [1-ACETYL-6-AMINO-3,] 3-dimethylindoline [1- (3,] 3-dimethyl-6-nitro-2, [3-DIHYDRO-INDOL-1-] yl) ethanone (250 mg) was dissolved in MeOH (20 mL), the mixture was bubbled with [H2] for 10 min. 10% Pd/C (50 mg) was added and the mixture was stirred under [H2] overnight. The mixture was filtered through Celte and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1: 1 EtOAc: CH2Cl2 to afford the title compound as a white crystalline material. MS: 205 [(M+1).] [CALC'D.] for C12H16N2O-204. 27. | |
With hydrogen;palladium 10% on activated carbon; In methanol; | l-(3,3-Dimethyl-6-nitro-2,3-dihydro-indol-l-yl)ethanone (250 mg) was dissolved in MeOH (20 mL), the mixture was bubbled with H2 for 10 min. 10% Pd/C (50 mg) was added and the mixture was stirred under H2 overnight. The mixture was filtered through Celite and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 1:1 EtOAc:CH2Cl2 to afford the title compound as a white crystalline material. MS: 205 (M+l). Calc'd. for Ci2H16N2O-204.27. | |
With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; at 50℃; under 2585.81 Torr; for 0.133333h; | A Parr hydrogenation unit was charged with l-(3,3-dimethyl-6-nitroindolin-1-yl)- ethanone (450 g, 1.92 mol), THF (1.8 L), and 10% Pd/C (20.3 g). The unit was purged with nitrogen twice then agitated. The unit was pressurized with 50 psi hydrogen and the agitation was continued until absorption ceased. Hydrogen absorption was exothermic. The temperature was maintained below 50 C during the reaction. The reaction was monitored by GC. After 8 min, the unit was purged with nitrogen. The mixture was filtered through a Celite pad and washed the pad with THF (100 mL x 1). The filtrate was concentrated under reduced pressure to 1A total volume and cooled to 0 C. To the mixture was added heptane (800 mL x 1) and the mixture was stirred at 0 C for 45 min. The resulting precipitate was collected by filtration, washed the solid with heptane (150 mL x 1), and dried at 50 C under reduced pressure to give l-(6-amino-3,3- dimethylindolin- 1 -yl)ethanone. |
Tags: 453562-68-0 synthesis path| 453562-68-0 SDS| 453562-68-0 COA| 453562-68-0 purity| 453562-68-0 application| 453562-68-0 NMR| 453562-68-0 COA| 453562-68-0 structure
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