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[ CAS No. 21557-09-5 ]

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2D
Chemical Structure| 21557-09-5
Chemical Structure| 21557-09-5
Structure of 21557-09-5 *Storage: {[proInfo.prStorage]}

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Product Details of [ 21557-09-5 ]

CAS No. :21557-09-5MDL No. :MFCD01075691
Formula : C12H15NO Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :189.25Pubchem ID :-
Synonyms :

Computed Properties of [ 21557-09-5 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 21557-09-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21557-09-5 ]

  • Downstream synthetic route of [ 21557-09-5 ]

[ 21557-09-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 123-75-1 ]
  • [ 403-42-9 ]
  • [ 21557-09-5 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; General procedure for the preparation of p-aminatedacetophenone (35a-35h) General procedure: To a solution of compounds 33 (10 mmol), 34a-34h(17 mmol) in dimethyl sulfoxide (25 mL), K2CO3(17 mmol) was added. The reaction was stirred at 90 °Cfor 24 h (35a, 35c, 35e, 35f) or 48 h (35d, 35g, 35h).After that, a saturated aqueous NaCl solution (50 mL) wasadded. Then, the reaction was extracted with ethyl acetate(8 × 25 mL), the organic phase was washed with saturatedaqueous NaCl solution (10 × 50 mL). The aqueous phasewas retro-extracted with ethyl acetate (2 × 25 mL). Organicphases were dried over anhydrous MgSO4 and the solventwas removed under reduced pressure. Compounds 35a, 35c,35e, 35f did not require further purification. Compounds35d, 35g, 35h were purified by column chromatography onsilica gel using hexane/ethyl acetate 8:2 as eluent.1-(4-(Pyrrolidin-1-yl)phenyl)ethanone (34a)Yield: 99%; light brown solid; 1H NMR (300 MHz,CDCl3) d 1.98-2.03 (m, 4H, 2CH2), 2.47 (s, 3H, CH3), 3.33(m, 4H, 2CH2), 6.48 (d, 2H, J 9.0 Hz, Ar-H), 7.83 (d, 2H,J 9.0 Hz, Ar-H); 13C NMR (75 MHz, CDCl3) d 25.4, 25.9,29.7, 110.6, 124.9, 130.7, 150.9, 196.3.
72.3% In water at 100℃; for 23h; Sealed tube;
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h;
With potassium carbonate
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h;
In dimethyl sulfoxide at 115℃; for 16h; Inert atmosphere;
In acetone at 180℃; for 3h; High pressure;
With potassium carbonate In dimethyl sulfoxide Reflux;
With potassium carbonate In dimethyl sulfoxide for 6h; Reflux;

Reference: [1]Barbosa, Sandro L.; Baroni, Adriano C. M.; Croda, Júlio; Gomes, Giovana B.; Guerrero, Palimécio G.; Moreira, Flora M. F.; Oliveira, Jefferson R. S.; Perdomo, Renata T.; Shiguemoto, Cristiane Y. K.; das Neves, Amarith R. [Journal of the Brazilian Chemical Society, 2020, vol. 31, # 6, p. 1284 - 1295]
[2]Soni, Rina; Hall, Thomas H.; Mitchell, Benjamin P.; Owen, Matthew R.; Wills, Martin [Journal of Organic Chemistry, 2015, vol. 80, # 13, p. 6784 - 6793]
[3]Mishra, Nidhi; Arora, Preeti; Kumar, Brajesh; Mishra, Lokesh C.; Bhattacharya, Amit; Awasthi, Satish K.; Bhasin, Virendra K. [European Journal of Medicinal Chemistry, 2008, vol. 43, # 7, p. 1530 - 1535]
[4]Location in patent: body text Zheng, Weihong; Degterev, Alexei; Hsu, Emily; Yuan, Junying; Yuan, Chengye [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 18, p. 4932 - 4935]
[5]Location in patent: experimental part Yadav, Neesha; Dixit, Sandeep K.; Bhattacharya, Amit; Mishra, Lokesh C.; Sharma, Manish; Awasthi, Satish K.; Bhasin, Virendra K. [Chemical Biology and Drug Design, 2012, vol. 80, # 2, p. 340 - 347]
[6]Watson, Andrew J. A.; Fairbanks, Antony J. [European Journal of Organic Chemistry, 2013, # 30, p. 6784 - 6788]
[7]Cvijetić, Ilija N.; Verbić, Tatjana Ž.; Ernesto de Resende, Pedro; Stapleton, Paul; Gibbons, Simon; Juranić, Ivan O.; Drakulić, Branko J.; Zloh, Mire [European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1474 - 1488]
[8]Ibrahim, Hany S.; Albakri, Mohamed E.; Mahmoud, Walaa R.; Allam, Heba Abdelrasheed; Reda, Ahmed M.; Abdel-Aziz, Hatem A. [Bioorganic Chemistry, 2019, vol. 85, p. 337 - 348]
[9]Allam, Heba Abdelrasheed; Fahim, Samar H.; F.Abo-Ashour, Mahmoud; Nocentini, Alessio; Elbakry, Mohamed E.; Abdelrahman, Mohamed A.; Eldehna, Wagdy M.; Ibrahim, Hany S.; Supuran, Claudiu T. [European Journal of Medicinal Chemistry, 2019, vol. 179, p. 547 - 556]
  • 2
  • [ 55-98-1 ]
  • [ 99-92-3 ]
  • [ 21557-09-5 ]
  • 3
  • [ 18711-13-2 ]
  • [ 21557-09-5 ]
  • 4,7-dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-1-yl)phenyl)ethyl)indolin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.5 g With diethylamine; at 20℃; for 24h; 4,7-Dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-l-yl)phenyl)ethyl)indolin-2-one (EXAMPLE 10): To <strong>[18711-13-2]4,7-dichloroindoline-2,3-dione</strong> (A) (12.5 g, 0.06 mol) in 800 mL of methanol were added l-(4-(pyrrolidin-l-yl)phenyl)ethanone (B) (45 g, 0.24 mol) and 0.5 mL of diethylamine (2). The reaction was stirred at rt for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CLLCn) to get 13.5 g of brown solid. It was purified again with flash chromatography using ethyl acetate/hexane to give 11.5 g of an off white solid. Repeating the reaction at the same scale to give another 11.5 g of product. Two batches of product were combined and recrystallized from methanol to get 20.5 g as an off white solid. 4,7-Dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-l- yl)phenyl)ethyl)indolin-2-one (EXAMPLE 10): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 1.96 (m, 4H), 3.30 (m, 4H), 3.65 (d, 1H, J=16 Hz), 4.29(d, 1H, J=16Hz), 6.34 (s, 1H), 6.53(d, 2H, J=8Hz), 6.88(d, 1H, J=8Hz), 7.28 (d, 1H, J=8Hz), 7.72 (d, 2H, J=8Hz), 10.97(s, 1H). Chiral separation was performed on under the following conditions. Preparatory method utilized the following:a RegisCell column L: 250 mm, IS: 50 mm, particle size: 5 mum; mobile phase: methanol/CO2, ratio: 35/65, detection wavelength: 254 nm, flow rate: 325 g/min, co-solvent flow rate 113.75 ml/min. Dissolved 19.72 g in 1000 ml of methanol, for a concentration of 0.020 g/ml. The injection volume was 25.00 ml for a total amount 0.500 g/injection. Yield was (+): 9.73 g, with optical rotation +247 at 20 C and (-): 9.26 g.
  • 4
  • [ 18711-13-2 ]
  • [ 21557-09-5 ]
  • (+)-4,7-dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-1-yl)phenyl)ethyl)indolin-2-one [ No CAS ]
  • (-)-4,7-dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-1-yl)phenyl)ethyl)indolin-2-one [ No CAS ]
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