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Chemical Structure| 92289-14-0 Chemical Structure| 92289-14-0

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Chemical Structure| 92289-14-0

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Product Details of [ 92289-14-0 ]

CAS No. :92289-14-0
Formula : C11H11NO6
M.W : 253.21
SMILES Code : O=C(O)CC(C1=CC=C([N+]([O-])=O)C=C1)CC(O)=O
MDL No. :MFCD11110458
InChI Key :YNPLFNKGJKRZNX-UHFFFAOYSA-N
Pubchem ID :18404630

Safety of [ 92289-14-0 ]

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

Application In Synthesis of [ 92289-14-0 ]

* 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 [ 92289-14-0 ]

[ 92289-14-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 92289-14-0 ]
  • [ 53911-69-6 ]
YieldReaction ConditionsOperation in experiment
70% With acetic anhydride; at 80℃; for 1h; b) 4-(4-Nitro-phenyl)-dihydro-pyran-2,6-dione A flask was charged with 20.0 g (79.0 mmol) of 3-(4-nitro-phenyl)-pentanedioic acid (as prepared in the previous step) and 22.4 mL (237 mmol) of acetic anhydride. The mixture was heated to 80 C. for 1 h, cooled to RT, and treated slowly with ether until the product began to precipitate. After allowing the solid to fully precipitate, the solid was filtered, washed with ether, and air-dried to afford 13.0 g (70%) of the title compound as an off-white solid: 1H-NMR (CDCl3; 400 MHz): δ 8.28 (d, 2H, J=8.8 Hz), 7.41 (d, 2H, J=8.8 Hz), 3.64-3.53 (m, 1H), 3.22-3.13 (m, 2H), 2.96-2.85 (m, 2H).
  • 3
  • [ 92289-14-0 ]
  • 3-(2,4-dinitro-phenyl)-glutaric acid [ No CAS ]
  • 4
  • [ 64-17-5 ]
  • [ 53911-69-6 ]
  • [ 92289-14-0 ]
  • 5
  • [ 126989-14-8 ]
  • [ 92289-14-0 ]
YieldReaction ConditionsOperation in experiment
88% With hydrogenchloride; water; at 100℃; for 22h;Product distribution / selectivity; g) 3-(4-Nitro-phenyl)-pentanedioic acid A suspension of 7.32 g (16.1 mmol) of 2,4-bis-ethoxycarbonyl-3-(4-nitro-phenyl)-pentanedioic acid diethyl ester (as prepared in the previous step) in concentrated HCl (15 mL) was heated to 100 C. for 22 h. The mixture was cooled to RT, and the resulting precipitate was filtered, washed with cold water, and air-dried to afford 3.58 g (88%) of the title compound as an off-white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.12 (d, 2H, J=8.8 Hz), 7.58 (d, 2H, J=8.8 Hz), 3.77-3.68 (m, 1H), 2.87-2.66 (m, 4H).
  • 6
  • [ 555-16-8 ]
  • [ 105-53-3 ]
  • [ 92289-14-0 ]
  • 8
  • 1-methyl-3-<4-nitro-phenyl>-cyclohexanol-(1)-one-(5)-dicarboxylic acid-(2.4)-diethyl ester [ No CAS ]
  • [ 92289-14-0 ]
  • 9
  • 4-hydroxy-6-oxo-4-methyl-2-<4-nitro-phenyl>-cyclohexane-dicarboxylic acid-(1.3)-diethyl ester [ No CAS ]
  • [ 92289-14-0 ]
  • 10
  • [ 92289-14-0 ]
  • [ 7783-06-4 ]
  • [ 7664-41-7 ]
  • [ 120066-99-1 ]
  • 11
  • [ 92289-14-0 ]
  • hydrogen trichloro-stannate(II) [ No CAS ]
  • [ 120066-99-1 ]
  • 12
  • [ 92289-14-0 ]
  • [ 7664-93-9 ]
  • [ 7697-37-2 ]
  • 3-(2,4-dinitro-phenyl)-glutaric acid [ No CAS ]
  • 13
  • [ 7647-01-0 ]
  • [ 126989-14-8 ]
  • [ 92289-14-0 ]
  • 14
  • [ 93711-15-0 ]
  • diluted KOH-solution [ No CAS ]
  • [ 92289-14-0 ]
  • 15
  • [ 92289-14-0 ]
  • [ 57-13-6 ]
  • [ 954124-21-1 ]
YieldReaction ConditionsOperation in experiment
61% at 160℃; for 1h; General procedure: 3-Phenylpentanedioic acid (5) (5.00 g, 24.01 mmol) and urea (3.60 g, 59.94 mmol) were mixed and heated at 160 C for 1 h. After being cooled, the reaction mixture was poured into water (20 mL). The solid was filtered off, washed with water and dried. Recrystallization from toluene gave 9 (3.26 g, 72%) as a white powder: mp 173-174 C; IR (KBr) cm-1 3184 (NH), 1734, 1686 (CO); 1H NMR (DMSO-d6) δ 10.86 (br s, 1H, NH which exchanges with D2O), 7.42-7.18 (m, 5H, aromatic), 3.50-3.35 (m, 1H, CH), 2.90-2.43 (m, 4H, CH2). Anal. (C11H11NO2) calcd: C 69.83, H 5.86, N 7.40; found: C 69.71, H 5.83, N 7.29.
22% at 150℃; for 0.666667h;Product distribution / selectivity; h) 4-(4-Nitro-phenyl)-piperidine-2,6-dione A mixture of 250 mg (0.987 mmol) of 3-(4-nitro-phenyl)-pentanedioic acid (as prepared in the previous step) and 119 mg (1.98 mmol) of urea was heated to 150 C. for 40 min (until all solid melted and gas evolution stopped). The mixture was cooled to RT, taken up in EtOAc (70 mL), washed with saturated aqueous NaHCO3 (2*40 mL), dried (MgSO4), and concentrated in vacuo to afford 52.0 mg (22%) of the title compound as a brown solid: 1H-NMR (CDCl3; 400 MHz): δ 8.28 (d, 2H, J=8.8 Hz), 7.44 (d, 2H, J=8.8 Hz), 3.64-3.54 (m, 1H), 3.04-2.96 (m, 2H), 2.86-2.76 (m, 2H).
  • 16
  • [ 4165-96-2 ]
  • [ 92289-14-0 ]
YieldReaction ConditionsOperation in experiment
94% a) 3-(4-Nitro-phenyl)-pentanedioic acid A flask charged with concentrated H2SO4 (400 mL) was cooled to 0 C. and treated with 50.0 g (240 mmol) of 3-phenyl-pentanedioic acid portionwise over 20 min and with fuming HNO3 (10 mL) dropwise over 20 min. The mixture was stirred at RT for 3 h, poured over ice (amount equivalent to 1000 mL), and the precipitate was filtered, washed with cold water, air-dried, and dried in a vacuum dessicator. The solid was triturated with a minimum amount of CH3CN, filtered, and air-dried. The filtrate was concentrated and triturated again with a minimum amount of CH3CN, filtered, and air-dried to afford a second batch. The two batches were combined to afford 56.9 g (94%) of the title compound as an off-white solid: 1H-NMR (DMSO-d6; 400 MHz): δ 8.15 (d, 2H, J=8.8 Hz), 7.58 (d, 2H, J=8.8 Hz), 3.62-3.50 (m, 1H), 2.79-2.57 (m, 4H).
  • 17
  • [ 92289-14-0 ]
  • [ 79-22-1 ]
  • [ 954124-21-1 ]
YieldReaction ConditionsOperation in experiment
43% Alternatively, the title compound can be obtained in the following manner: A solution of 500 mg (1.97 mmol) of 3-(4-nitro-phenyl)-pentanedioic acid (as prepared in the previous step) in 50 mL dioxane was cooled to 10 C. and treated with 229 μL (2.96 mmol) of methyl chloroformate and 936 μL (6.71 mmol) of triethylamine for 7.2 h. A solution of 0.5 M ammonia in dioxane (15.8 mL, 7.90 mmol) was added at 10 C. and the mixture stirred at RT for 72 h. The mixture was filtered through Celite, the filter cake washed with EtOAc, and the solvents were evaporated in vacuo. The residue was treated with solid 1.30 g (15.8 mmol) of NaOAc and acetic anhydride (4 mL) and heated to 100 C. for 1 h. The mixture was cooled to RT and concentrated to half the original volume. The residue was taken up in EtOAc (100 mL), washed with saturated aqueous NaHCO3 (1×75 mL), brine (1×75 mL), and water (1×75 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 50-60% EtOAc-hexane afforded 197 mg (43%) of the title compound as an off-white solid (see spectrum above).
  • 18
  • [ 1123-49-5 ]
  • [ 555-16-8 ]
  • [ 92289-14-0 ]
  • 19
  • [ 92289-14-0 ]
  • (7-nitro-2-oxo-1,2,3,4-tetrahydro-[4]quinolyl)-acetic acid [ No CAS ]
  • 20
  • [ 92289-14-0 ]
  • 3-(2,4-diamino-phenyl)-glutaric acid [ No CAS ]
  • 21
  • [ 64-17-5 ]
  • [ 92289-14-0 ]
  • diethyl 3-(4-nitro-phenyl)-glutarate [ No CAS ]
  • 22
  • [ 159088-58-1 ]
  • [ 108-24-7 ]
  • [ 92289-14-0 ]
  • 23
  • [ 92289-14-0 ]
  • [ 954124-21-1 ]
  • 24
  • [ 92289-14-0 ]
  • [ 74-89-5 ]
  • [ 954124-90-4 ]
  • 25
  • [ 92289-14-0 ]
  • [ 1312808-99-3 ]
  • 26
  • [ 92289-14-0 ]
  • [ 1312809-00-9 ]
  • 27
  • [ 92289-14-0 ]
  • [ 1312809-17-8 ]
  • 28
  • [ 92289-14-0 ]
  • [ 1312809-18-9 ]
  • 29
  • [ 92289-14-0 ]
  • [ 1616787-08-6 ]
YieldReaction ConditionsOperation in experiment
100% With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 3h;Inert atmosphere; Step 1 In a round bottom flask purged with N2, containing 3-(4-Nitro-phenyl)-pentanedioic acid (45, 110 mg, 0.434 mmol) in 5 mL of anhydrous DCM was added Oxalyl Chloride (0.911 mmol, 0.082 mL). To this solution was added 1 drop of N,N-dimethylformamide. The reaction mixture was stirred for 3 hours and concentrated in vacuo to afford (46) as a white solid (125 mg, 0.434 mmol, quantitative). LCMS, taken in methanol: m/z 282.0 [M+H+, for bis methanolysis product].
With tin(ll) chloride; In dichloromethane; at 20℃;Reflux; SOCl2 (0.45mL, 6mmol) was added to a suspension of diacid 5 (0.506g, 2mmol) in dry CH2Cl2 (20mL) while stirring at room temperature. After 2h, the mixture was heated under reflux overnight. The solvent was removed under reduced pressure and the diacid chloride 6 was directly used in the next step without further purification.
With thionyl chloride; In dichloromethane; at 20℃; for 2h; SOCl2 (0.45 mL,6 mmol) was added to a suspension of diacid 5 (0.506 g, 2 mmol) in dry CH2Cl2 (20 mL) while stirring at room temperature. After 2 h, the mixture was heated under reflux overnight. The solvent was removed under reduced pressure and the diacid chloride 6 was directly used in the next step without further purification.
  • 32
  • [ 92289-14-0 ]
  • [ 1616787-07-5 ]
  • 33
  • [ 340265-92-1 ]
  • [ 92289-14-0 ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydroxide; In water; for 3h;Reflux; Compound 4 (45 mmol) was dissolved in a mixture of distilled water (67.5 mL) and sodium hydroxide (67.5 g). The resulting mixture was refluxed vigorously for 3 h, and then cooled to room temperature and poured into water (340 mL). The resulting mixture was extracted with ether (2x100 mL). The water phase was acidified with concentrated hydrochloric acid (190 mL). The precipitated glutaric acid was removed by filtration and washed with cold water to remove sodium chloride. The acid was recrystallized from water and dried in vacuum to give a pale brown solid (6.84 g), 60% yield, mp 236-237 C. 1H NMR (400 MHz, CDCl3) δ/ppm: 12.20 (s, 2H), 8.15 (d, J=6.9 Hz, 2H), 7.57 (d, J=6.9 Hz, 2H), 3.60-3.50 (m, 1H), 2.73 (dd, J=8.1-8.1 Hz, 2H), 2.60 (dd, J=8.1-8.1 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ/ppm: 172.9, 152.1, 146.6, 129.4, 123.7, 39.9, 38.3; FTIR (cm-1): 3209, 2983, 2933, 2907, 1696, 1607, 1515, 1402, 1347, 1311, 1286, 1250, 1220, 1186, 1162, 1118, 884, 862, 849, 753, 698. Anal. Calcd for C11H11NO6: C, 52.18; H, 4.38; N, 5.53. Found: C, 52.16; H, 4.40; N, 5.57.
60% With water; sodium hydroxide; at 100℃; for 3h; Compound 4 (45 mmol) was dissolved in a mixture of distilled water (67.5 mL) and sodium hydroxide (67.5 g). The resulting mixture was refluxed vigorously for 3 h, and then cooled to room temperature and poured into water (340 mL). The resulting mixture was extracted with ether (2x100 mL). The water phase was acidified with concentrated hydrochloric acid (190 mL). The precipitated glutaric acid was removed by filtration and washed with cold water to remove sodium chloride. The acid was recrystallized from water and dried in vacuum to give a pale brown solid (6.84 g), 60% yield, mp 236-237 C .1H NMR (400 MHz, CDCl3) d/ppm: 12.20 (s, 2H), 8.15 (d, J6.9 Hz,2H), 7.57 (d, J6.9 Hz, 2H), 3.60e3.50 (m,1H), 2.73 (dd, J8.1e8.1 Hz,2H), 2.60 (dd, J8.1e8.1 Hz, 2H); 13C NMR (100 MHz, CDCl3) d/ppm:172.9, 152.1, 146.6, 129.4, 123.7, 39.9, 38.3; FTIR (cm1): 3209, 2983,2933, 2907,1696,1607,1515,1402,1347,1311,1286,1250,1220,1186,1162, 1118, 884, 862, 849, 753, 698. Anal. Calcd for C11H11NO6: C,52.18; H, 4.38; N, 5.53. Found: C, 52.16; H, 4.40; N, 5.57.
  • 34
  • [ 92289-14-0 ]
  • [ 1616787-09-7 ]
  • 35
  • [ 92289-14-0 ]
  • 1-(4-[3,4-bis(2,5-dimethyl-3-thienyl)cyclopent-3-en-1-yl]phenyl)-2,5-di-2-thienyl-1H-pyrrole [ No CAS ]
 

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