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[ CAS No. 142314-70-3 ] {[proInfo.proName]}

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Chemical Structure| 142314-70-3
Chemical Structure| 142314-70-3
Structure of 142314-70-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 142314-70-3 ]

CAS No. :142314-70-3 MDL No. :MFCD18432396
Formula : C9H7NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 209.16 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 142314-70-3 ]

* 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 [ 142314-70-3 ]

[ 142314-70-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 61940-21-4 ]
  • [ 142314-70-3 ]
YieldReaction ConditionsOperation in experiment
54% With 4-methylmorpholine N-oxide; In acetonitrile; at 20℃; for 20h; Step 3) Synthesis of methyl 2-formyl-6-nitrobenzoate (4) Methyl 2-(bromomethyl)-6-nitrobenzoate (3; 3.9 g, 14.0 mmol) was taken up in 100 mL of CH3CN along with 4 A sieves (20.0 g). N-methylmorpholine oxide (2.0 g, 170.0 mmol) was added and the resulting reaction mixture was stirred at room temperature for 20 h (slight exotherm, used an ice bath for cooling). The reaction was filtered and the filtrate was concentrated under reduced pressure. Purification by chromatography (1:1 pentane/EtOAC) afforded methyl 2-formyl-6-nitrobenzoate 4 as a light yellow solid (2.5 g, 54% yield). MS (ESI) calcd for C9H7NO5; 209.03. found: 210 [M+H].
With 4-methylmorpholine N-oxide; In acetonitrile; at 20℃; for 1.5h;Molecular sieve; To a stirring suspension of flame-dried 4 A molecular sieves in CH3CN (50 mL) was added NMO (2.9 g, 25 mmol). After 5 min, the benzyl bromide (Step B, 3.1 g, 11 mmol) in CH3CN (5 mL) was added. The reaction was stirred at RT for 1.5 h, filtered through silica gel, eluted with EtOAc and concentrated in vacuo to give a reddish brown oil. Purification by silica flash chromatography (0-30% EtOAc:hexane) gave the desired aldehyde as a white solid
With 4-methylmorpholine N-oxide; In acetonitrile; at 20℃; for 20h;Molecular sieve; Step 3) Synthesis of methyl 2-formyl-6-nitrobenzoate (4): Methyl 2-(bromomethyl)-6-nitrobenzoate (3; 3.9 g, 14.0 mmol) was taken up in 100 mL of CH3CN along with 4 A sieves (20.0 g). N-methylmorpholine oxide (2.O g, 170.0 mmol) was added and the resulting reaction mixture was stirred at room temperature for 20 h (slight exotherm, used an ice bath for cooling). The reaction was filtered and the filtrate was concentrated under reduced pressure. Purification by chromatography (1 :1 pentane/EtOAC) afforded methyl 2-formyl-6- nitrobenzoate 4 as a light yellow solid (2.5 g, 54 % yield). MS (ESI) calcd for C9H7NO5; 209.03; found: 210 [M + H].
  • 2
  • [ 142314-70-3 ]
  • [ 36600-66-5 ]
  • [ 846055-77-4 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; acetic acid; at 200℃; for 0.333333h;Microwave irradiation; A solution of the aldehyde (Step C, 0.58 g, 3.3 mmol), 4-t-butylphenylhydrazine-HCl (0.66 g, 3.3 mmol), AcOH (1 mL), and dioxane (3 mL) in a sealed reaction vial was heated at 200° C. for 20 min in a microwave. Upon cooling, the residue was diluted with EtOAc (10 mL), then hexane (10 mL). The resulting precipitate was filtered to afford the desired compound as a tan solid. MS m/e 324 (M+H)+. Calc'd for C18H17N3O3- 323.35.
  • 3
  • [ 61940-22-5 ]
  • [ 142314-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / 1,2-dichloro-ethane / 8 h / Reflux 2: 4-methylmorpholine N-oxide / acetonitrile / 1.5 h / 20 °C / Molecular sieve
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