5-Nitroisatin

orange-yellow to orange crystalline powder

5-Nitroisatin is a member of indoles. It has a role as an anticoronaviral agent.

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with NaGeneral procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 °C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).A solution of NaNO3 (5.78 g, 0.068 mol) in concentrated H2SO4 (100 mL) was added drop wise, with stirring, to a solution of isatin 3h (10.0 g, 0.068 mol) in concentrated H2S04 (120 mL) for a period of 1 h at 0 °C. Then the reaction mixture was poured into ice water (750 mL), the precipitate was collected by filtration and washed with water to give 22a. Yield 11. 88 g, 91percent.A mixture of compound 10 (10g, 0.068mol) and 100ml of HWeigh isatin5.00g (33.98mmol), potassium nitrate 3.44g (33.98mmol), in which case stirredslowly 15mL dissolved in 20mL, concentrated sulfuric acid, respectively, andthen at 0 ~ -4 , the isatin concentrated sulfuric acidsolution was slowly added dropwise a solution of potassium nitrate inconcentrated sulfuric acid, after the addition was complete stirring wascontinued for 30min, and then stirred at room temperature 10min, TLC thereaction was complete, the mixture was poured into ice-water, stirred for30min, suction filtered to give a yellow solid, dried under vacuum oven to givethe desired product 5-nitro-indole-dione 5.72g, yield 87.6percent.-5 conditions, 5.9 g of isatin (II) were weighed in batches dissolved in 26 mL of cold concentrated sulfuric acid, A mixture of 2 mL of fuming nitric acid and 3 mL of concentrated sulfuric acid was slowly added dropwise, And the reaction temperature was controlled around 0 ° C, After completion of the reaction, the reaction was continued for 3 hours.After completion of the reaction, the mixture was poured into a beaker containing 100 g of crushed ice, Filtration, ice water washing to neutral, The filter cake was dried to yield 6.4 g of the orange-red product (III) in 83.4percent yield, The 5-nitroisatin (1) was prepared according to the reported literature refPreviewPlaceHolder[25]. Briefly, in a mixture of 50 g (35 mL, 0.50 mol) of conc. nitric acid and 74 g (40 mL, 0.75 mol) conc. sulfuric acid, isatin (48.50 g, 0.33 mol) was added slowly with frequent shaking in 500 mL round bottomed flask. Then the mixture was cooled by immersing the flask in crushed ice cold water. After adding all isatin, flask was fitted with reflux condenser and the mixture was heated on water bath maintaining the temperature at 60 °C for 1 h to obtain the desired compound 5-nitroisatin (1). Then the entire content was then transferred into a beaker containing 500 mL cold water, stirred in order to wash out as much acid from the desired product. When compound 1 settled completely to the bottom, the upper acid layer was removed from the mixture. Then the bottom layer was transferred to the separating funnel and shaked vigorously with about 50 mL of water. Then the residual layer was collected, dried with anhydrous calcium chloride and finally filtered to obtain the pure compound (1). Yield 65percent, Mp 230 °C; IR (KBr) cmCompound indoline-2, 3-dione (48.5 g, 0.33 mol) was added into a mixture of 50 g (35 mL, 0.5 mol) of conc. nitric acid and 74 g (40 mL, 0.75 mol) conc. sulfuric acid with frequent shaking in 500-mL round bottomed flask, keeping the mixture cool by immersing the flask in ice cold water. After adding all indoline-2, 3-dione, flask was fitted with reflux condenser and the mixture was heated on water bath maintaining the temperature at 60 °C for 1 h to obtain the desired compound 5-nitroindoline-2, 3-dione (1). Content was then poured into a beaker containing 500 mL cold water, stirred in order to wash out as much acid from the desired compound. When compound (1) completely settled to the bottom, the upper acid liquor was completely poured off from the mixture. Then the residual liquid was transferred to the separating funnel and shaked vigorously with about 50 mL of water. Bottom layer was collected, dried with anhydrous calcium chloride and finally filtered to obtain the pure compound (1). Yield 62percent, mp 230 °C. IR (KBr) cmThe solution of isatin (52.09 g, 0.352 mol) in 520 mL of concentrated sulfuric acid was cooled down by ice bath to 0 General procedure: 4.2 General procedure for the synthesis of 5 and 10a–g: (a) A 500 ml, three-necked, round-bottomed flask fitted with a condenser and a thermometer was charged with chloral hydrate (16.50 g, 0.1 mol) and 220 ml of water. Then anhydrous sodium sulfate (15.00 g), aniline derivative (0.1 mol), HCl solution (5.2 percent, 70 ml), and hydroxylamine hydrochloride (20.81 g, 0.3 mol, in 95 ml of water) were added in successively. After being heated to reflux for 1 h, the reaction mixture was cooled to room temperature. The intermediate compound (anilide derivative) was collected by filtration and dried, which was used for next step without further purification. (b) A 100 ml, three-necked, round-bottomed flask fitted with a thermometer was charged with concentrated sulfuric acid (10 equiv). After heating to 50 °C with stirring, the dried product (1 equiv) from the above step was added in over a period of 20 min. The resulting solution was heated to 65 °C and kept for 1 h and then cooled down to room temperature with an ice bath. The precipitate was filtered out and dried to get the target compounds. The dried product from the above step (20.5 g, 0.098 mol) was added into concentrated sulfuric acid (53 ml) in a period of 20 min at 50 °C. Then the resulted mixture was heated to 65 °C and kept for 1 h. The mixture was poured into ice water. The precipitate in the mixture was filtered out and dried

For the preparation of potential antibacterial and antifungal agents, spiro[indole-thiazol 4-one] as an important drug framework, potential antimycobacterial agents, antispasmodic agents, human glutamine transferase inhibitors, Insect repellent, anti-HIV agent, antibacterial agent, potential anti-tuberculosis agent and acetylcholinesterase inhibitor, etc.

Molecular Weight:192.13
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:192.01710661
Monoisotopic Mass:192.01710661
Topological Polar Surface Area:92
Heavy Atom Count:14
Complexity:309
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes