7-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3percent HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.General procedure: Isatins (1a–j, 3.0 g), hydrazine hydrate (80percent, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 °C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L−1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a–j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.To a freshly prepared mixture of 1-bromo-2-nitro-benzene acetic acid (1.98 g, 7.61 mmol) in EtOH (20 mL) and 9M H2SO4 (20 mL) at 50° C. was added Zn dust( 2.00 g, 30.6 mmol) at ambient temperature. The reaction was stirred for 30 minutes at ambient temperature and then at 70° C. for 30 minutes. The reaction was cooled to ambient temperature and poured into H2O (100 mL) and estracted with EtOAc (2.x.50 mL). The combined organic Layers were dried (Na2SO4), filtered and evaporated to give a crude brown residue. Chromatography on silica gel eluting with a gradient EtOAc-hexane system (1:10 to 1:1) gave the intermediate title compound (0.43 g, 27percent) as a light brown solid. Analysis Theory: C, 45.31; H, 2.85; N, 6.60 Found: C, 45.01; H, 2.55; N, 6.42General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3percent HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.General procedure: Isatins (1a–j, 3.0 g), hydrazine hydrate (80percent, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 °C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L−1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a–j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.To a freshly prepared mixture of 1-bromo-2-nitro-benzene acetic acid (1.98 g, 7.61 mmol) in EtOH (20 mL) and 9M H2SO4 (20 mL) at 50° C. was added Zn dust( 2.00 g, 30.6 mmol) at ambient temperature. The reaction was stirred for 30 minutes at ambient temperature and then at 70° C. for 30 minutes. The reaction was cooled to ambient temperature and poured into H2O (100 mL) and estracted with EtOAc (2.x.50 mL). The combined organic Layers were dried (Na2SO4), filtered and evaporated to give a crude brown residue. Chromatography on silica gel eluting with a gradient EtOAc-hexane system (1:10 to 1:1) gave the intermediate title compound (0.43 g, 27percent) as a light brown solid. Analysis Theory: C, 45.31; H, 2.85; N, 6.60 Found: C, 45.01; H, 2.55; N, 6.42General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.General procedure: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.To a solution of Via (2.5 g, 11.061 mmol) in ethanol (50 mL), hydrazine hydrate (99%, 0.5 mL) was added and the mixture was refluxed under nitrogen atmosphere for 30 min. Formed yellow precipitate was isolated by filtration, and suspended in anhydrous ethanol. Potassium tertiary butoxide (4.03 g, 35.90 mmol) was added to the above suspension. The mixture was refluxed for 2h. After the completion of reaction, mixture was poured over ice-water, acidified with dil. HC1 to pH 2. Mixture was extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and evaporated under reduced pressure to get crude of VIb (0.89 g) which was taken for the next step without any purificationTo a cooled (-78C) solution of To the suspension of VIb (200mg, 0.94 mmol) in water (5 mL) and sodium hydroxide (56mg, 1.41 mmol) was added dimethyl sulphate (178mg, 1.41 mmol) and the mixture was heated at 100 oC for lh. After the consumption of starting material, reaction mixture was cooled to 0 oC, added water and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and evaporated under reduced pressure. So obtained crude was purified by column chromatography by using 10% ethyl acetate in pet-ether to get pure Vic (180 mg).

Molecular Weight:212.04
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:210.96328
Monoisotopic Mass:210.96328
Topological Polar Surface Area:29.1
Heavy Atom Count:11
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes