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Chemical Structure| 59803-35-9

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Product Details of [ 59803-35-9 ]

CAS No. :59803-35-9
Formula : C14H17NO6
M.W : 295.29
SMILES Code : O=C(OCC)C(CC1=CC=CC=C1[N+]([O-])=O)C(OCC)=O
MDL No. :MFCD00110674
InChI Key :XKWHIUXRQYXRSG-UHFFFAOYSA-N
Pubchem ID :309274

Safety of [ 59803-35-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 59803-35-9 ]

* 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 [ 59803-35-9 ]

[ 59803-35-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 7647-01-0 ]
  • [ 59803-35-9 ]
  • [ 2001-32-3 ]
  • 2
  • [ 59803-35-9 ]
  • [ 2001-32-3 ]
YieldReaction ConditionsOperation in experiment
94% In a single necked round-bottomed flask (2 L), step-a product (8.7g, 0.029 mol), hydrochloric acid (131 mL, 6N) and acetic acid (131 mL) were charged. The reaction mixture was refluxed for 48 hours. The progress of the reaction was checked by TLC. The reaction mixture was basified with sodium hydroxide (500 mL, 6M) and was extracted with ethyl acetate (3 x 250 mL). The organic part was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel: 100-200 mesh, eluent: 40% ethyl acetate in hexane) to afford the pure compound (5.4 g, 94 % yield).
With hydrogenchloride; In water; acetic acid; for 48h;Heating / reflux; A solution of crude diethyl (2-nitrobenzyl) malonate in 6N aqueous HC1 (15 ml) and acetic acid (15 ml) was stirred at refluxing temperature for 48 hours. After cooled to ambient temperature, the mixture was concentrated under reduced pressure. To the residue was added 10% aqueous NaOH solution and washed with ethyl acetate. The aqueous layer was acidified with aqueous HC1 solu- tion, and the mixture was extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure to obtain 3- (2-nitrophenyl) propanoic acid. 'H NMR (CDC13) 8 2.79 (t, J= 7.6 Hz, 2H), 3.24 (t, J= 7.6 Hz, 2H), 7. 38-7. 44 (m, 2H), 7.55 (dt, J= 7.6, 1.6 Hz, 1H), 7.96 (dd, J= 7.6, 1.6 Hz, 1H).
With hydrogenchloride; water; acetic acid; for 48h;Heating / reflux; To a solution of 2-nitrobenzyl bromide (1.00 g, 4.63 mmol) and diethyl malonate (0.741 g, 4.63 mmol) in 30 ml of hexane was added potassium carbonate (0.640 g, 4.63 mmol) and 18- Crown-6 (0.012 g, 0.05 mmol). After stirred at 80 C for 18 hours, the mixture was diluted with water and was extracted with ethyl acetate. The organic layer was washed with water, then with brine, and concentrated under reduced pressure to obtain crude diethyl (2-nitrobenzyl) malonate. A solution of crude diethyl (2-nitrobenzyl) malonate in 6N aqueous HC1 (15 ml) and acetic acid (15 ml) was stirred at refluxing temperature for 48 hours. After cooled to ambient temperature, the mixture was concentrated under reduced pressure. To the residue was added 10% aqueous NaOH solution and washed with ethyl acetate. The aqueous layer was acidified with aqueous HCl solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure to obtain 3- (2-nitrophenyl) propanoic acid. 'H NMR (CDC13) 8 2.79 (t, J= 7.6 Hz, 2H), 3.24 (t, J= 7.6 Hz, 2H), 7. 38-7. 44 (m, 2H), 7.55 (dt, J= 7.6, 1.6 Hz, 1H), 7.96 (dd, J= 7.6, 1.6 Hz, 1H). A solution of 3- (2-nitrophenyl) propanoic acid (1.20 g, 6.15 mmol) and thionyl chloride (0. 878 g, 7.38 mmol) in dichloromethane (5 ml) was stirred and heated to reflux for 2 hours. The mixture was concentrated under reduced pressure to obtain 3- (2-nitrophenyl) propanoyl chloride. To the obtained crude 3- (2-nitrophenyl) propanoyl chloride (1.31 g, 6.15 mmol) was added CS2, and aluminum trichloride (1.07 g, 8. 0 mmol) was added portionwise at 0C. The mixture was stirred at 70C for 3 hours, and after cooled to ambient temperature, water was added and extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane : ethylacetate 10: 1) to afford 4-nitroindan-1-one (0.44 g). 'H NMR (CDC13) 8 2.79-2. 82 (m, 2H), 3.64-3. 66 (m, 2H), 7.62 (t, J= 7.9 Hz, 1H), 8.09 (d, J= 7.6 Hz, 1H), 8.47 (d, J= 8.2 Hz, 1H). To a solution of 4-nitroindan-1-one (0.381 g, 2.15 mmol) in ethanol (5 ml) was added sodium borohydride (0.048 g, 1.29 mmol) at 0 C, and the mixture was stirred at room temperature for 3 hours. Aqueous solution of ammonium chloride was added to the mixture, and extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure to obtain 4-nitroindan-1-ol. 'H NMR (CDC13) 8 1.90 (d, J= 6. 5 Hz, 1H), 2.00-2. 07 (m, 1H), 2.56-2. 63 (m, 1H), 3.25-3. 33 (m, 1H), 3.54-3. 60 (m, 1H), 5. 30-5. 35 (m, 1H), 7.44 (t, J= 8.2 Hz, 1H), 7.72 (d, J = 7.6 Hz, 1H), 8. 12 (d, J= 8. 2 Hz, 1H). A solution of 4-nitroindan-1-ol (0.385 g, 2.15 mmol) and p-toluenesulfonic acid (5. 0 mg, 0.03 mmol) in toluene (30 ml) was stirred and heated to reflux for 16 hours. After cooled to ambient temperature, the mixture was washed with aqueous sodium bicarbonate solution. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure. The obtained residue was purified by preparatory TLC (hexane: ethylacetate 3: 1) to afford 7-nitro-lH- indene (0.289 g). 'H NMR (CDC13) 8 3.94 (s, 2H), 6.75 (dt, J= 5. 7,1. 9 Hz, 1H), 6.93 (dt, J= 5. 7,1. 6 Hz, 1H), 7.45 (t, J= 8. 2 Hz, 1H), 7.68 (d, J= 7.6 Hz, 1H), 8. 05 (d, J= 8.2 Hz, 1H). To a solution of 2, 3-dimethyl-2-butene (21.5 mg, 0.31 mmol) in THF (2 ml) at 0C was added borane-THF (0.307 ml, 0.31 mmol) dropwise. After stirred for lhour at 0C, 7-nitro-1H-indene (45.0 mg, 0.28 mmol) in THF (5 ml) was added dropwise, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled to 0C, and water (0.15 ml), 4N aqueous sodium hydroxide (0.45 ml), and 30% H202 (0. 45ml) were added. The mixture was then warmed to room temperature and poured into water, extracted with ethyl acetate and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. To the obtained mixture in toluene (1 ml) was added acetic anhydride (40.8 mg, 0.40 mmol) and pyridine (0.4 ml), and then stirred for 16 hours at room temperature. The mixture was concentrated under reduced pressure, and the obtained residue was purified by preparatory TLC (hexane: ethylacetate 2: 1) to obtain 4-nitro-2, 3-dihydro-lH-inden-2-yl acetate (16.0 mg). 'H NMR (CDC13) 8 2.03 (s, 3H), 3.12 (dd, J= 17. 5,1. 6 Hz, 1H), 3.40 (dd, J= 17. 5, 6. 3 Hz, 1H), 3.60 (dd, J= 19. 2,2. 2 Hz, 1H), 3.74 (dd, J= 19. 2,6. 6 Hz, 1H), 5.58-5. 62 (m, 1H), 7.39 (t, J= 7.9 Hz, 1H), 7.54 (d, J = 7.3 Hz, 1H), 8.06 (d, J = 8.2 Hz, 1H). To a mixture of 4-nitro-2, 3-dihydro-lH-inden-2-yl acetate (100 mg, 0.45 mmol) and ammonium chloride (100 mg) in ethanol (6 ml) and water (3 ml) was added iron powder (300 mg) portionwise at room temperature. The mixture was stirred at 90 C for 1 hour, and after cooled to room temperature, the mixture was dil...
 

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