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Chemical Structure| 1079992-97-4 Chemical Structure| 1079992-97-4

Structure of 1079992-97-4

Chemical Structure| 1079992-97-4

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Product Details of [ 1079992-97-4 ]

CAS No. :1079992-97-4
Formula : C9H8FNO4
M.W : 213.16
SMILES Code : O=C(OC)C1=C(F)C=CC([N+]([O-])=O)=C1C
MDL No. :MFCD28347723
InChI Key :VSAHHNFBEGJLEX-UHFFFAOYSA-N
Pubchem ID :59334469

Safety of [ 1079992-97-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1079992-97-4 ]

* 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 [ 1079992-97-4 ]

[ 1079992-97-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1079992-96-3 ]
  • [ 74-88-4 ]
  • [ 1079992-97-4 ]
YieldReaction ConditionsOperation in experiment
56% With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 16.0h; Step B: Preparation of methyl 6-fluoro-2-methyl-3-nitrobenzoate: To a mixture of 6-fluoro-2-methyl-3-nitrobenzoic acid (21.2 g, 0.107 mol), powdered potassium carbonate (36.8, 0.266 mol) in DMF (200 mL) was added methyl iodide (37.8 g, 0.266 mol). The mixture was stirred at ambient temperature for 16 hours, then diluted with water and extracted with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography (20% ethyl acetate/hexane) afforded 12.6 g (56%) of the title compound.
With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 12.0h; Reference Example 46 methyl 6-fluoro-2-methyl-3-nitrobenzoate A crudely purified product (20.7 g) of 6-fluoro-2-methyl-3-nitrobenzoic acid was dissolved in N,N-dimethylformamide (208 mL), and potassium carbonate (28.7 g, 208 mmol) and iodomethane (8.45 mL, 135 mmol) were added at room temperature. The reaction solution was stirred at room temperature for 12 hr, and poured into water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound as a crudely purified product (21.0 g, yield 95%). 1H-NMR (CDCl3) δ: 2.53 (3H, s), 3.99 (3H, s), 7.11 (1H, t, J = 8.6 Hz), 8.01 (1H, dd, J = 9.0, 5.0 Hz).
With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20.0℃; To a stirred solution of 2-fluoro-6-methylbenzoic acid (Description 16,20 g, 130 mmol) in conc. sulfuric acid (160 ml) at-15C was added a mixture of fuming nitric acid (7 ml) in conc. sulfuric acid (30 ml). The reaction mixture was warmed to 0C and stirred at this temperature for 30 minutes. The mixture was poured onto ice/water and stirred for 10 minutes, then extracted with ethyl acetate (3 x 200 ml). The combined organic layers were washed with brine, dried over NA2SO4, filtered and evaporated. The residue was dissolved in anhydrous N, N-DIMETHYLFORMAMIDE (250 ml) and potassium carbonate (35.9 g, 260 mmol) added followed by iodomethane (10.5 ml, 169 mmol), and the resulting mixture stirred at room temperature overnight. The reaction was poured into water (1 litre) and extracted with ethyl acetate (3 x 200 ml). The combined organic layers were washed with water (3 x 400 ml), brine (200 ml), dried over NA2SO4, filtered and evaporated. The residue was dissolved in methanol (300 ml), flushed with nitrogen and 10% palladium on carbon (3 g) added. The mixture was hydrogenated at 50 psi until H2 uptake ceased. The catalyst was removed by filtration and the filtrate evaporated to give the title compound (13.6 g, 57%). 1H NMR (500 MHz, CDC13) 8 2.11 (3H, s), 3.92 (3H, s), 6.65 (1H, dd, J 8. 7 and 4.9), 6. 78 (1H, T, J9. 0).
  • 2
  • [ 1079992-97-4 ]
  • [ 848678-60-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;palladium on activated carbon; In methanol; for 12.0h; Reference Example 47 methyl 3-amino-6-fluoro-2-methylbenzoate To a solution of a crudely purified product (27.7 g, 130 mmol) of <strong>[1079992-97-4]methyl 6-fluoro-2-methyl-3-nitrobenzoate</strong> in methanol (260 mL) was added palladium carbon (6.00 g, 10wt%) and the mixture was stirred under hydrogen atmosphere for 12 hr. The catalyst was filtered off through celite, the filtrate was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (ethyl acetate/hexane=1/1) to give the title compound (15.0 g, yield 63%). 1H-NMR (CDCl3) δ: 2.13 (3H, s), 3.56 (2H, br s), 3.93 (3H, s), 6.67 (1H, d, J = 8.8, 4.8 Hz), 6.80 (1H, t, J = 8.8 Hz).
With hydrogen;palladium 10% on activated carbon; In methanol; under 2585.81 Torr; To a stirred solution of 2-fluoro-6-methylbenzoic acid (Description 16,20 g, 130 mmol) in conc. sulfuric acid (160 ml) at-15C was added a mixture of fuming nitric acid (7 ml) in conc. sulfuric acid (30 ml). The reaction mixture was warmed to 0C and stirred at this temperature for 30 minutes. The mixture was poured onto ice/water and stirred for 10 minutes, then extracted with ethyl acetate (3 x 200 ml). The combined organic layers were washed with brine, dried over NA2SO4, filtered and evaporated. The residue was dissolved in anhydrous N, N-DIMETHYLFORMAMIDE (250 ml) and potassium carbonate (35.9 g, 260 mmol) added followed by iodomethane (10.5 ml, 169 mmol), and the resulting mixture stirred at room temperature overnight. The reaction was poured into water (1 litre) and extracted with ethyl acetate (3 x 200 ml). The combined organic layers were washed with water (3 x 400 ml), brine (200 ml), dried over NA2SO4, filtered and evaporated. The residue was dissolved in methanol (300 ml), flushed with nitrogen and 10% palladium on carbon (3 g) added. The mixture was hydrogenated at 50 psi until H2 uptake ceased. The catalyst was removed by filtration and the filtrate evaporated to give the title compound (13.6 g, 57%). 1H NMR (500 MHz, CDC13) 8 2.11 (3H, s), 3.92 (3H, s), 6.65 (1H, dd, J 8. 7 and 4.9), 6. 78 (1H, T, J9. 0).
  • 3
  • [ 90259-27-1 ]
  • [ 1079992-97-4 ]
  • 4
  • [ 1079992-97-4 ]
  • methyl 2-(bromomethyl)-6-fluoro-3-nitrobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 38.0h;Reflux; Methyl 6-fluoro-2-methyl-3-nitrobenzoate 500 mg (2.35 mmol),N-Bromosuccinimide 418 mg (2.35 mmol)Was dissolved in 11.7 mL of degassed carbon tetrachloride, and thenAdd 23 mg (0.070 mmol) of benzoyl peroxide andIt was refluxed for 38 hours.After cooling to room temperature, the precipitate was filtered off, and the filtrate was distilled off under reduced pressure.The obtained solid was purified by silica gel column chromatography.Methyl 2- (bromomethyl) -6-fluoro-3-nitrobenzoate was obtained in a yield of 421 mg and a yield of 62%.The compound data of methyl 2- (bromomethyl) -6-fluoro-3-nitrobenzoate is shown below.
  • 5
  • [ 1079992-97-4 ]
  • 3-(7-fluoro-4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione [ No CAS ]
  • 6
  • [ 1079992-97-4 ]
  • 3-(4-amino-7-fluoro-1-oxoisoindolin-2-yl)piperidine-2,6-dione [ No CAS ]
 

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