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Chemical Structure| 30836-96-5 Chemical Structure| 30836-96-5

Structure of 30836-96-5

Chemical Structure| 30836-96-5

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Product Details of [ 30836-96-5 ]

CAS No. :30836-96-5
Formula : C10H6N2O4
M.W : 218.17
SMILES Code : O=C(C1=NC2=CC=C([N+]([O-])=O)C=C2C=C1)O
MDL No. :MFCD08436460
InChI Key :CFOGTLCSNDGABE-UHFFFAOYSA-N
Pubchem ID :12324258

Safety of [ 30836-96-5 ]

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 [ 30836-96-5 ]

* 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 [ 30836-96-5 ]

[ 30836-96-5 ] Synthesis Path-Downstream   1~10

  • 2
  • 2-benzylidene-6-nitroquinoline [ No CAS ]
  • [ 30836-96-5 ]
YieldReaction ConditionsOperation in experiment
39% With potassium permanganate; In pyridine; water; The starting material was prepared as follows: To a solution of 2-benzylidene-6-nitroquinoline (4.9 g; 17.7 mM) in pyridine (36.6 ml) and water (8 ml) was added portion wise KMnO4 (7.5 g; 47.8 mM) keeping the temperature between 18 and 20 C. After filtration on celite, the solution was acidified (pH3), at 0 C., with H2SO4 (65%). The resulting precipitate was filtered, washed with water and ether and then dried to give 2-carboxy-6-nitroquinoline (1.5 g; 39%). NMR (DMSO-d6 +CF3 COOD): δ8.26 (d, 1H); 8.36 (d, 1H); 8.54 (dd, 1H); 8.90 (d, 1H); 9,17 (d, 1H). MS (CI+): 219 (M+H).
  • 3
  • [ 30836-96-5 ]
  • [ 157915-32-7 ]
YieldReaction ConditionsOperation in experiment
71% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; To a solution of 2-carboxy-6-nitroquinoline (1.5 g; 6.8 mM) in THF (30 ml) was added triphenylphosphine (2.7 g; 10.2 mM), allyl alcohol (0.7 ml; 10.2 mM) and DEAD (1.63 ml; 10.2 mM). After stirring at ambient temperature for 30 minutes, the mixture was extracted with ethyl acetate and purified by subjecting to flash chromatography, eluding with ethyl acetate/petroleum ether (40/60) to give 2-allyloxycarbonyl-6-nitroquinoline (1.2 g; 71%). NMR (CDCCl3): δ5.0-5.03 (m, 2H); 5.35-5.55 (m, 2H); 6.07-6.20 (m, 1H); 8.34 (d, 1H); 8.47 (d, 1H); 8.52-8.59 (m, 2H); 8.86 (d, 1H).
  • 4
  • [ 613-30-9 ]
  • [ 30836-96-5 ]
YieldReaction ConditionsOperation in experiment
With selenium(IV) dioxide; In pyridine; at 70.0℃; for 16h; To the reactor, 2-methyl-6-nitroquinoline 20.0 g and 80 mL of pyridine, and then added 13g of selenium dioxide stirred, heated to 70 C for 16 hours. Filtered, rinsed with dichloromethane, and 22g of brown-red solid crude product was obtained after spinning off pyridine.
  • 5
  • [ 67-56-1 ]
  • [ 30836-96-5 ]
  • [ 112089-59-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 25.0℃; for 12h;Cooling with ice; To the reactor, add 6-nitroquinoline-2-carboxylic acid crude product 22g and 150mL methanol, ice bath drops add 23mL thionyl chloride, drip to 25 C stirred for 12 hours. 300mL of water was added to quench the reaction, and after the methanol was removed, the ethyl acetate 3×300mL of the extract was extracted, and the organic phase was washed three times with saturated sodium bicarbonate aqueous solution, and the water and saturated saline were washed three times each. After drying and filtering, spin dry to obtain 23g of reddish-brown solid crude.
  • 6
  • [ 100-01-6 ]
  • [ 30836-96-5 ]
  • 7
  • [ 30836-96-5 ]
  • [ 100-36-7 ]
  • N-(2-(diethylamino)ethyl)-6-nitroquinoline-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.8 g In the reactor, add 22 g of 6-nitroquinoline-2-carboxylic acid crude product, 200 mL of N,N-dimethylformamide and N,N,N',N'-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate 48.5g,Under argon protection, 41.2 g of N,N-diisopropylethylamine was added dropwise to an ice bath,After stirring for 1 hour, 17.6 g of N,N-diethylethylenediamine was added dropwise, and the temperature was raised to 25 C. and stirred for 12 hours after the dropping.The reaction was stopped, 500 mL of water was added, extracted with 500 mL×3 of ethyl acetate, the combined organic layers were washed three times with 5% aqueous citric acid solution, and then washed three times with saturated aqueous sodium bicarbonate solution and saturated brine respectively,It was filtered, dried, and subjected to column chromatography (dichloromethane:methanol=20:1) to obtain 24.8 g of a brown solid with a two-step yield of 74%.
  • 8
  • [ 30836-96-5 ]
  • 2,5-dioxopyrrolidin-1-yl (2-((2-(diethylamino)ethyl)carbamoyl)quinolin-6-yl)carbamate [ No CAS ]
  • 9
  • [ 30836-96-5 ]
  • [ 112089-60-8 ]
  • 10
  • [ 30836-96-5 ]
  • 6-amino-N-[2-(diethylamino)ethyl]-2-quinolinecarboxamide [ No CAS ]
 

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