Home Cart Sign in  
Chemical Structure| 15379-41-6 Chemical Structure| 15379-41-6

Structure of 15379-41-6

Chemical Structure| 15379-41-6

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 15379-41-6 ]

CAS No. :15379-41-6
Formula : C11H13NO
M.W : 175.23
SMILES Code : O=C1N(CCC)C2=C(C=CC=C2)C1
MDL No. :MFCD06662368

Safety of [ 15379-41-6 ]

Application In Synthesis of [ 15379-41-6 ]

* 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 [ 15379-41-6 ]

[ 15379-41-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 41042-12-0 ]
  • [ 15379-41-6 ]
YieldReaction ConditionsOperation in experiment
81% With hydrazine hydrate; at 130℃; for 4h; No. A3-167: 1-(3,4-Dichlorophenyl)-N-(2′-oxo-1′-propyl-1′,2′-dihydrospiro[cyclopropane-1,3′-indol]-5-yl)methanesulfonamide (0134) (0135) In a round-bottom flask under argon, isatin (5.00 g, 34 mmol) was dissolved in N,N-dimethylformamide (50 ml), and 1-iodopropane (11.56 g, 68 mmol) and potassium carbonate (9.39 g, 68 mmol) were added. The resulting reaction mixture was stirred at room temperature for 6 h, and water and ethyl acetate were then added. The aqueous phase was then extracted repeatedly with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave <strong>[41042-12-0]1-propyl-1H-indole-2,3-dione</strong> (6.10 g, 93% of theory). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.59 (m, 2H), 7.11 (m, 1H), 6.89 (d, 1H), 3.71 (t, 2H), 1.76 (sext, 2H), 1.00 (t, 3H). Subsequently, <strong>[41042-12-0]1-propyl-1H-indole-2,3-dione</strong> (6.10 g, 32 mmol) was heated together with hydrazine hydrate (30.96 g, 612 mmol) at 130 C. for 4 h, and after cooling to room temperature the mixture was added to ice-water. The aqueous phase was subsequently extracted repeatedly with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1-propyl-1,3-dihydro-2H-indol-2-one (4.50 g, 81% of theory). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.28 (m, 2H), 7.02 (m, 1H), 6.84 (d, 1H), 3.68 (t, 2H), 3.52 (s, 2H), 1.71 (sext, 2H), 0.97 (t, 3H). In the next step, 1-propyl-1,3-dihydro-2H-indol-2-one (3.90 g, 22 mmol) was, at a temperature of 15 C., dissolved together with 1,2-dibromoethane (6.27 g, 33 mmol) in a mixture of abs. tetrahydrofuran (25 ml) and abs. N,N-dimethylformamide (1 ml), followed by careful addition, a little at a time, of sodium hydride (2.76 g, 69 mmol, 60% strength dispersion) and stirring under reflux conditions for 1 h. After cooling to room temperature, methanol and water were added to the reaction mixture. The aqueous phase was extracted intensively with ethyl acetate and the combined organic phases were additionally washed in each case once with saturated sodium carbonate solution and water. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1′-propylspiro[cyclopropane-1,3′-indol]-2′(1′H)-one (4000 mg, 89% of theory). 1H-NMR (400 MHz, CDCl3 δ, ppm) 7.22 (m, 1H), 7.00 (m, 1H), 6.92 (d, 1H), 6.83 (d, 1H), 3.75 (t, 2H), 1.74 (m, 2H), 1.50 (m, 2H), 1.26 (m, 2H), 0.98 (t, 3H). 1′-Propylspiro[cyclopropane-1,3′-indol]-2′(1′H)-one (5.20 g, 21 mmol) was added to glacial acetic acid (35 ml), and fuming nitric acid (7 ml) was then added slowly and carefully. The resulting reaction mixture was stirred at room temperature for 2 h and then slowly diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate, and the combined organic phases were washed with saturated sodium carbonate solution and then dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5′-nitro-1′-propylspiro[cyclopropane-1,3′-indol]-2′(1′H)-one (3600 mg, 71% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.26 (dd, 1H), 7.73 (d, 1H), 6.98 (d, 1H), 3.30 (t, 2H), 1.87 (m, 2H), 1.75 (sext, 1H), 1.68 (m, 2H), 1.00 (t, 3H). In the next step, 5′-nitro-1-propylspiro[cyclopropane-1,3′-indol]-2′(1′H)-one (3.60 g, 15 mmol) and tin(II) chloride dihydrate (13.19 g, 58 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80 C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5′-amino-1′-propylspiro[cyclopropane-1,3′-indol]-2′(1′H)-one (3100 mg, 98% of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 δ, ppm) 6.71 (d, 1H), 6.58 (dd, 1H), 6.25 (d, 1H), 3.71 (t, 2H), 1.73 (m, 2H), 1.42 (m, 2H), 1.25 (m, 2H), 0.98 (t, 3H). Under argon, 5′-amino-1′-propylspiro[cyclopropane-1,3′-indol]-2′(1′H)-one (100 mg, 1.0 equiv.) and (3,4-dichlorophenyl)methanesulfonyl chloride (168 mg, 1.4 equiv.) were dissolved in abs. acetonitrile in a round-bottom flask, pyridine (0.08 ml, 2.1 equiv.) and dimethyl sulfoxide (0.04 ml, 0.60 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under redu...
81% With hydrazine hydrate; for 3h;Reflux; General procedure: Isatin (0.1 mol, 14.7 g) was dissolved in DMF (60 mL) and finely ground anhydrous K2CO3 (0.15 mol,20.7 g) was added under stirring. RX (0.15 mol) was added dropwise and mixture was heated at 60-70C for 3 h (as alkylation reagent RX were used Me2SO4, EtI, n-PrBr, AmBr, BnCl, PMBCl,respectively). After cooling to room temperature mixture was poured into ice water (200 mL).Precipitated orange solid was filtereted, washed with water and recrystallized from ethanol (95%) togive N-alkylated isatins as red crystalls in 37-92% yield. The purity of obtained compounds weredetermined by melting points, which corresponded to those published in the literature (ref. 2-4).N-Substituted isatin (10 mmol) was mixed with 16 M N2H4·H2O (15 mL). The suspension was heatedat reflux 3 h (caution: rapid gas evolution), then it was cooled to room temperature, diluted with waterS4(40 mL) and extracted with EtOAc (3 x 25 mL). Organic phase was washed with water (25 mL), brine (25 mL), then it was dried over Na2SO4 and evaporated under reduced pressure to give the desired product. The latter was recrystallized from hexane and small amount of EtOAc to give N-substituted indolin-2-one as yellow solid in 47-96% yield. The purity of obtained compounds were determined by melting points and 1H NMR spectra data, which corresponded to those published in the literature (ref. 5,6).N-Substituted indolin-2-one (2 mmol) were dissolved in dry DMF (5 mL) and NaH (60% dispersion in mineral oil, 6 mmol, 240 mg) was portionwise added carefully at a temperature of -15 C. When the rapid evolution of H2 stops, the mixture allowed to stir for 10 min. Then solution of 1,2-dibromoethane (508 mg, 2.7 mmol) in dry DMF (3 mL) was added to the mixture. The latter was warmed to room temperature and stirred overnight. Then it was cooled with ice, diluted with water (20 mL) and extracted with PhMe (2 x 15 mL). Organic phase was washed with water (2 x 15 mL), brine (15 mL) and then it was dried over Na2SO4. Evaporation under reduced pressure gave the desired product. The latter was washed with hexane to remove mineral oil or purified by flash column chromatography (eluent: hexane/CH2Cl2). The spiro[cyclopropane-1,3'-indolin]-2'-ones 1 are yellow solids, except N-amyl substituted spiro[cyclopropane-1,3'-indolin]-2'-one, which is brown liquid. The purity of obtained compounds were determined by 1H NMR spectra data. Corresponding cyclopropanes were previously known in the literature (ref. 7-11).
 

Historical Records

Technical Information

Categories