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[ CAS No. 193977-99-0 ] {[proInfo.proName]}

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Chemical Structure| 193977-99-0
Chemical Structure| 193977-99-0
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CAS No. :193977-99-0 MDL No. :
Formula : C10H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 190.20 Pubchem ID :-
Synonyms :

Safety of [ 193977-99-0 ]

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Application In Synthesis of [ 193977-99-0 ]

* 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 [ 193977-99-0 ]

[ 193977-99-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6146-52-7 ]
  • [ 75-03-6 ]
  • [ 193977-99-0 ]
YieldReaction ConditionsOperation in experiment
97.2% Stage #1: 5-Nitro-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 25℃; for 2h; 4.1.13. Preparation of 1-ethyl-5-nitro-1H-indole (a11) To a solvent of DMF (150 mL) was added 60% NaH (12 g, 0.3 mol)under stirring at 25 C. The mixture was added the mixture of 5-nitro-1H-indole a10 (20 g, 0.12 mol) in DMF slowly at 0 . After the gasescaped, iodoethane (15 mL, 0.18 mol) was added under stirring at 25 Cfor 2 h. When completed, to a solution of saturated NH4Cl (600 mL) wasadded the reaction mixture under stirring for 20 min. Then, the mixturewas filtered and the residue was dried to obtain the yellow solid a11 in97.2% yield. MS (ESI) m/z: 191.3 [M+H]+.
92% With potassium carbonate In N,N-dimethyl-formamide at 5 - 60℃; for 12h; Inert atmosphere; Cooling with ice; 1.1 Step 1 Synthesis of intermediate 1A A 100 ml four-necked flask was flushed with nitrogen, and 4.87 g (3.0 × 10-2 mol) of the following indole 1 and 8.30 g (6.0 × 10-2 mol) of potassium carbonate and 30.0 g of dimethylformamide were added, Stirring was performed at 5 ° C. on an ice bath.Thereto was added dropwise 6.11 g (3.6 × 10-2 mol) of ethyl iodide.After completion of dropping, the mixture was heated and stirred at 60 ° C. for 12 hours on an oil bath.After cooling to room temperature, it was poured into 50.0 g of ion exchange water.The solution was transferred to a separatory funnel and extracted with ethyl acetate.The organic layer was washed twice with ion-exchanged water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure.The following intermediate 1A was obtained with 5.26 g in a yield of 92%.
80% With potassium hydroxide In propan-2-one at 20℃; for 0.25h;
71.3% With potassium carbonate In N,N-dimethyl-formamide at 20℃; 95 ethyl iodide (289 mg, 1.85 mmol) was added in one portion to a stirred solution of 5-nitro-1H-indole (250 mg, 1.542 mmol) and potassium carbonate (426 mg, 3.08 mmol) in DMF (5 mL) at room temperature. The resulting brown suspension was poured into water (50 mL), and the resulting precipitate was collected by vacuum filtration and dried in vacuo at 40 °C to a constant weight. l-ethyl-5-nitro-1H-indole was isolated as a pale yellow solid (0.220 g, 71.3%) : N M R (400 MHz, DMSO-c e) δ 8.57 (d, J = 2.3 Hz, 1H), 8.03 (dd, J = 9. 1, 2.3 Hz, 1H), 7.74 - 7.65 (m, 2H), 6.76 (d, J = 3.2 Hz, 1H), 4.30 (q, J = 7.2 Hz, 2H), 1.38 (t, J = 7.2 Hz, 3H) ; 13C NMR ( 101 MHz, DMSO-de) δ 140.61 , 138.27, 131.90, 127.33, 117.53, 116.23, 110.18, 103.59, 40.85, 40.17, 39.96, 39.75, 39.54, 39.33, 39. 13, 38.92, 15.34; ESIMS m/z 191 ( [M + H]+ ).
Stage #1: 5-Nitro-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Inert atmosphere; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;
With potassium hydroxide In acetonitrile at 80℃; for 6h; 5.2. Synthesis of intermediate 10a-10f General procedure: Compounds 9a-9b (1.0 mmol, 1.0 eq), iodomethane, iodoethane orbenzyl chloride (2.0 mmol, 2.0 eq) and KOH (1.0 mmol, 1.0 eq) wereadded into 10 mL of acetonitrile and then stirred at 80 C for 6 h. Then,the mixtures were concentrated under reduced pressure to give crudeproducts, which were then purified by silica gel column chromatographyusing PE/EA (4/1, v/v) as eluents to get intermediate 10a-10f.

  • 2
  • [ 74-96-4 ]
  • [ 6146-52-7 ]
  • [ 193977-99-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydride In N,N-dimethyl-formamide at 20℃;
99% Stage #1: 5-nitroindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h; Stage #2: ethyl bromide With sodium iodide In N,N-dimethyl-formamide; mineral oil at 0℃; 1 4.1.1 1-Ethyl-5-nitro-1H-indole (1) Into a two-necked 100mL round-bottomed flask, 0.666g (27.75mmol) of NaH, 60% dispersion in mineral oil, was placed and washed with toluene (3×10mL). With stirring, a solution of commercial 5-nitroindole, 1,500g (9.25mmol) in 5mL of anhydrous DMF was dropped into the flask, and the initial yellow color changed to red with the formation of H2 gas. After 40minat room temperature, the mixture was cooled to 0°C, and 2.00mL (26.61mmol, d=1.46g/mL) of bromoethane was dropped into the flask, followed by 0.050g of NaI. The reaction was monitored by TLC analysis (eluent toluene/n-hexane/ethyl acetate, 1:1:1). At the end of the reaction, 25mL of water was added, and the solvent was evaporated under reduced pressure, leaving a residue, which was extracted with ethyl acetate (3×30mL). The organic phase, washed with water, brine, and dried over anhydrous Na2SO4, was concentrated under vacuum giving 1.69g of a yellow solid. Yield: 99%; Rf: 0.63 (toluene/n-hexane/ethyl acetate, 1:1:1); mp=94°C; 1H NMR (300MHz, DMSO-d6): δ 7.74 (d, J=2.1Hz, 1H, H-4), 7.20 (dd, J=9.0, 2.1Hz, 1H, H-6), 6.87 (m, 2H, H-7 e H-3), 5.93 (d, J=3.3Hz, 1H, H-2), 3.47 (q, J=7.1Hz, 2H, CH2), 0.55 (t, J=7.1Hz, 3H, CH3), ppm; HRMS (ESI-MS, 140eV): m/z [M+H]+ calculated for C10H11N2O2+, 191.2035; found, 191.1859.
93.7% Stage #1: 5-nitroindole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h; Stage #2: ethyl bromide With sodium iodide In N,N-dimethyl-formamide; mineral oil 2 4.1.1 General procedure for the synthesis of 1N-Substituted nitroindoles (1-4) General procedure: As a typical procedure, the synthesis of 5-nitro-1-octadecyl-1H-indole 1 is described in detail. Into a two-necked 100mL round-bottomed flask, 0.333g (13.88mmol) of NaH, 60% dispersion in mineral oil, was placed and washed with toluene (3×10mL). With stirring, a solution of commercial 5-nitroindole, 0.750g (4.625mmol), in 5mL of anhydrous DMF, was dropped into the flask, and the initial yellow color changed to red with the formation of H2 gas. After 40minat room temperature, the mixture was cooled to 0°C, and 2.36mL (6.94mmol, d=0.849g/mL) of 1-chlorooctadecane was dropped into the flask and 0.050g of NaI were added to the mixture. The reaction was monitored by TLC analysis (eluent toluene/n-hexane/ethyl acetate, 1:1:1). At the end of the reaction, 25mL of water was added, and the solvent was evaporated under reduced pressure, leaving a residue that was extracted with ethyl acetate (3×50mL). The organic phase, washed with water and brine and dried over anhydrous Na2SO4, was concentrated under vacuum giving a crude yellow solid (2.522g). This crude product was purified with a silica gel chromatographic column (d 3cm, l 35cm, 230-400 mesh, eluent n-hexane/toluene, 1:1), yielding 1.618g of a pure yellow powder.
With sodium hydride In toluene Reflux;

  • 3
  • [ CAS Unavailable ]
  • [ 1010-19-1 ]
  • [ 193977-99-0 ]
YieldReaction ConditionsOperation in experiment
93% With Cs2CO3 In toluene at 120℃; for 18h; Sealed tube; Inert atmosphere;
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