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Chemical Structure| 114741-27-4

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Product Details of [ 114741-27-4 ]

CAS No. :114741-27-4
Formula : C10H10N2O2
M.W : 190.20
SMILES Code : CC(NC1=CC2=C(NC(C2)=O)C=C1)=O

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Application In Synthesis of [ 114741-27-4 ]

* 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.

  • Downstream synthetic route of [ 114741-27-4 ]

[ 114741-27-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 20876-36-2 ]
  • [ 114741-27-4 ]
YieldReaction ConditionsOperation in experiment
46% In water; acetic anhydride; Example 159c N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide A mixture of 200 mg (1.35 mmol) of 5-amino 1,3-dihydro-indol-2-one in 6 ml of acetic anhydride was refluxed for 30 minutes. The reaction mixture was poured onto 50 g of crushed ice. The mixture was stirred well and the solid was collected by vacuum filtration. The solid was washed with 200 ml of H2O and air dried to yield N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (119 mg, 46percent): 1H NMR (DMSO-d6): delta1.97 (s, 3H), 3.41 (s, 2H), 6.68 (d, J=8.4 Hz, 1H),), 7.26 (dd, J1=2 Hz, J2=8.4 Hz, 1H), 7.46 (d, J=2 Hz, 1H), 9.73 (s, 1H). 10.23 (s, 1H), ESI-MS: m/z 189 (m-H)-.
  • 2
  • [ 20876-36-2 ]
  • [ 75-36-5 ]
  • [ 114741-27-4 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine; In tetrahydrofuran; at -30 - 20℃; 5-Amino-1,3-dihydro-indol-2-one 30c (3.5 g, 23.6 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with triethylamine (3.6 ml, 26 mmol) to the solution at room temperature. Upon completion of the addition, the mixture was cooled down to -30° C. in a dry ice-acetone bath, and added slowly with acetyl chloride (1.8 ml, 24.8 mmol) while maintaining the temperature below -20° C. Upon completion of the addition, the dry ice-acetone bath was removed, and the reaction mixture was allowed to warm up to room temperature and stirred for 20 minutes.After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ethyl acetate (20 ml), gray solids were formed and filtered. The filter cake was washed with water (70 ml.x.3) to obtain 2.5 g of solids. The filtrate was extracted with ethyl acetate (200 ml.x.3). The combined organic extracts were concentrated under reduced pressure, combined with the above solids to obtain the title compound N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide 30d (4.0 g, yield 89percent) as a gray solid.MS m/z (ESI): 191.2 [M+1]
89% With triethylamine; In tetrahydrofuran; at -30 - 20℃; 5-Amino-1,3-dihydro-indol-2-one 30c (3.5 g, 23.6 mmol) was dissolved in 20 ml of tetrahydrofuran under stirring, and added with triethylamine (3.6 ml, 26 mmol) to the solution at room temperature. Upon completion of the addition, the mixture was cooled down to -30°C in a dry ice-acetone bath, and added slowly with acetyl chloride (1.8 ml, 24.8 mmol) while maintaining the temperature below -20°C. Upon completion of the addition, the dry ice-acetone bath was removed, and the reaction mixture was allowed to warm up to room temperature and stirred for 20 minutes. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ethyl acetate (20 ml), gray solids were formed and filtered. The filter cake was washed with water (70 ml.x.3) to obtain 2.5 g of solids. The filtrate was extracted with ethyl acetate (200 ml.x.3). The combined organic extracts were concentrated under reduced pressure, combined with the above solids to obtain the title compound N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide 30d (4.0 g, yield 89percent) as a gray solid. MS m/z (ESI): 191.2[M+1]
88.9% With triethylamine; In tetrahydrofuran; at -30 - 20℃; A stirred solution of <strong>[20876-36-2]5-amino-1,3-dihydro-indol-2-one</strong> (3.5 g, 23.6 mmol, prepared according to U.S. Pat. No. 6,114,371) in 20 ml of tetrahydrofuran was added with triethylamine (1.3 ml, 9 mmol). The solution was cooled down to -30° C. in an acetone-dry ice bath and added with acetyl chloride (1.3 ml, 9 mmol) dropwise. Upon the completion of the addition, the resulting mixture was stirred for 20 minutes at room temperature and added with ethyl acetate (20 ml) until precipitate was formed. The solid was filtered, washed with water (50 ml.x.3) and dried in vacuo to give N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (4 g, 88.9percent) as a white solid.MS m/z (ESI): 191 [M+1].
88.9% With triethylamine; In tetrahydrofuran; at -30 - 20℃; for 0.333333h; A stirred solution of 5-amino-l,3-dihydro-indol-2-one (3.5 g, 23.6 mmol, prepared according to US6114371) in 20 ml of tetrahydrofuran was added with tirethylamine (1,3 ml, 9 mmol). The solution was cooled down to -30°C in an acetone-dry ice bath and added with acetyl chloride (1.3 ml, 9 mmol) drop wise. Upon the completion of the addition, the resulting mixture was stirred for 20 minutes at room temperature and added with ethyl acetate (20 ml) until precipitate was formed. The solid was filtered, washed with water (50 mix 3) and dried in vacuo to give N-(2-oxo-2,3-dihydro-lH-indol-5-yl)-acetamide (4 g, 88.9percent) as a white solid. MS m/z (ESI) : 191[MH-I].

  • 3
  • [ 20876-36-2 ]
  • [ 108-24-7 ]
  • [ 114741-27-4 ]
YieldReaction ConditionsOperation in experiment
85% With trimethylamine; In tetrahydrofuran;Reflux; General procedure: The mixture of <strong>[20876-36-2]5-amino-2-oxindole</strong> 2d, triethylamine and RCOCl (oracetic anhydride for 2e) in THF (2 mL) was refluxed for 1?15 h withTLC control. After reaction complete the mixture was cooled down toroom temperature, the precipitate formed was filtered, washed withethyl acetate and dried on air. The following compounds were obtainedaccording to method A:4.1.2.1. 5-Acetamido-2-oxindole (2e) (Method A). The reaction of <strong>[20876-36-2]5-amino-2-oxindole</strong> 2d (0.5 g, 0.003 mol), trimethylamine (0.49 mL,0.004 mol) and acetic anhydride (0.41 mL, 0.003 mol) in THF (2 mL)for 1 h gave 5-acetamido-2-oxindole 2e as light-gray powder with yield85percent (0.47 g). Mp (exp)=170?173 °C; [FoundC10H10N2O2*0.5AcOH*0.5H2O: C, 57.90; H, 5.44; N, 12.33 requiresC, 57.63; H, 5.44; N, 12.22percent]; nmax (vaseline oil) 3160?3310 (br) 1710,1670 cm?1;dH (400 MHz, DMSO?d6): 2.00 (3H, s, CH3), 3.44 (2H, s, CH2), 6.72(1H, d, J 8.3, CHAr), 7.30 (1H, dd, J 2.2, 8.3, CHAr), 7.49 (1H, s, CHAr),9.78 (1H, s, NH), 10.27 (1H, s, NH)
 

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