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Chemical Structure| 128156-55-8 Chemical Structure| 128156-55-8

Structure of 128156-55-8

Chemical Structure| 128156-55-8

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Product Details of [ 128156-55-8 ]

CAS No. :128156-55-8
Formula : C10H9NO3
M.W : 191.18
SMILES Code : O=C(C1=C2N=C(C)OC2=CC=C1)OC
MDL No. :MFCD25978082

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Application In Synthesis of [ 128156-55-8 ]

* 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 [ 128156-55-8 ]

[ 128156-55-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 89942-77-8 ]
  • [ 91-66-7 ]
  • [ 17672-21-8 ]
  • [ 128156-55-8 ]
  • 2
  • [ 17672-21-8 ]
  • [ 24057-28-1 ]
  • [ 75-36-5 ]
  • [ 128156-55-8 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In m-xylene; 3rd Stage Preparation of Methyl 2-methylbenzoxazole-4-carboxylate To a solution of the methyl (2-amino-3-hydroxy)benzoate (3 g; 18.01 mM) in m-xylene (150 ml) was added acetyl chloride (1.518 ml; 21.6 mM). A precipitate was formed; this was left to stir for 30 minutes. On the addition of triethylamine (2.97 ml; 21.6 mM) the solution became translucent. Pyridinium-p-toluene sulphonic acid (1.2 g; 21.6 mM) was added, and the mixture refluxed for 34 hours. The solvent was removed by distillation (vacuum) to yield a brown solid which was column chromatographed (50% ethyl acetate/50% petrol 60/80) to give the desired product as a yellow solid.
  • 3
  • [ 17672-21-8 ]
  • [ 75-36-5 ]
  • [ 128156-55-8 ]
YieldReaction ConditionsOperation in experiment
79% With pyridine; toluene-4-sulfonic acid; triethylamine; In xylene;Reflux; A solution of <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (167 mg, 1.0 mmol), acetyl chloride (86 mg, 1.1 mmol) and triethylamine (101 mg, 1.1 mmol) in xylene (10 mL) was stirred at 0C for 2 h. Pyridine (20 mg, 0.25 mmol) and TsOH (43 mg, 0.25 mmol) were then added and the mixture was heated at reflux overnight. The mixture was then cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water, brine, then dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography using petroleum ether/ethyl acetate 5:1 (v:v) as eluent to give methyl 2- methylbenzo[d]oxazole-4-carboxylate (151 mg, 79%). LC-MS (ES-API); rt 8.08 min; m/z calculated for C10H9NO3 [M+H]+ 192.1 , found 192.1.
  • 4
  • [ 17672-21-8 ]
  • [ 78-39-7 ]
  • [ 128156-55-8 ]
YieldReaction ConditionsOperation in experiment
at 120℃; for 16h; A solution of 563 <strong>[17672-21-8]methyl 2-amino-3-hydroxybenzoate</strong> (1 g, 5.98 mmol) in 564 1,1,1-triethoxyethane (17.7 g, 109 mmol) was heated at 120 C. for 16 hours. The mixture was concentrated. The residue was purified by flash silica gel chromatography (ethyl acetate/petroleum ether gradient 030%) to afford 565 methyl 2-methylbenzo[d]oxazole-4-carboxylate.
 

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