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Chemical Structure| 35748-34-6 Chemical Structure| 35748-34-6

Structure of 35748-34-6

Chemical Structure| 35748-34-6

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Product Details of [ 35748-34-6 ]

CAS No. :35748-34-6
Formula : C8H9NO3
M.W : 167.16
SMILES Code : O=C(OC)C1=CC=CC(N)=C1O
MDL No. :MFCD09842614
InChI Key :OMWQHVRUXLRZRC-UHFFFAOYSA-N
Pubchem ID :12782444

Safety of [ 35748-34-6 ]

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

Application In Synthesis of [ 35748-34-6 ]

* 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 [ 35748-34-6 ]

[ 35748-34-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 35748-34-6 ]
  • [ 4385-76-6 ]
  • [ 1175530-02-5 ]
YieldReaction ConditionsOperation in experiment
71% With pyridine; In toluene; at 0 - 70℃; Example 159 Bmethyl 2-hydroxy-3-(4-(pyridin-4-yl)benzamido)benzoate; Thionyl chloride (10 mL) was added to <strong>[4385-76-6]4-(pyridin-4-yl)benzoic acid</strong> (1.6 g, 8 mmol) and the mixture was stirred under reflux overnight. The solvent was evaporated under reduced pressure and the residue was dried in vacuum giving 4-(pyridin-3-yl)benzoyl chloride. To a solution of methyl 3-amino-2-hydroxybenzoate (1 g, 6 mmol) and pyridine (480 mg, 6 mmol) in toluene (50 mL) was added 4-(pyridin-3-yl)benzoyl chloride (1.3 g, 6 mmol) portion wise at 0° C. and then stirred at 70° C. for 4 h. The resulting mixture was extracted with ethyl acetate (100 mL.x.4), the organic phase was washed with water and saturated sodium bicarbonate, dried with anhydrous sodium sulfate and evaporated under reduced pressure to obtain methyl 2-hydroxy-3-(4-(pyridin-4-yl)benzamido)benzoate as yellow solid (1.5 g, yield 71percent). 1H-NMR (400 MHz, CDCl3) delta 4.00 (s, 3H), 6.97-7.01 (t, J=8.2 Hz, 1H), 7.57-7.63 (m, 3H), 7.78-7.80(d, J=8.0 Hz, 2H), 8.05-8.07 (d, J=8.8 Hz, 2H), 8.67-8.78 (m, 4H), 11.44(s, 1H); LC-MS (ESI) m/z: 349 (M+1)+.
  • 2
  • [ 35748-34-6 ]
  • [ 122-51-0 ]
  • [ 1086378-35-9 ]
YieldReaction ConditionsOperation in experiment
91% With ytterbium(III) triflate; In toluene; at 100℃; for 1.0h;Microwave irradiation; Methyl 3-amino-2-hydroxybenzoate (1.69 g, 10.13 mmol) was suspended in toluene (2 mL) in a microwave vial. HC(OEt)3 (1.80 g, 12.15 mmol) and Yb(OTf)3 (0.003 g, 0.005 mmol) was added and the reaction was heated at 100 C for 1 hour in the microwave. The reaction mixture was evaporated and purified by flash chromatography (petroleum ether/EtOAc 4:1) to give the title compound (1.63 g, 91%) as pale yellow crystals. mp. 116 - 118 C (Litt9. 77 C). 1H NMR (300 MHz, CDCl3) delta 8.21 (s, 1H), 8.04 (dd, J = 7.8, 1.2 Hz, 1H), 7.99 (dd, J = 8.0, 1.2 Hz, 1H), 7.44 (dd, J = 8.0, 7.8 Hz), 3.76 (s, 3H). 13C NMR (75 MHz, CDCl3) delta 180.9, 164.4, 153.4, 141.4, 128.0, 125.6, 124.5, 115.4, 52.6
  • 3
  • [ 35748-34-6 ]
  • [ 149-73-5 ]
  • [ 1086378-35-9 ]
YieldReaction ConditionsOperation in experiment
93% With toluene-4-sulfonic acid; for 1.0h;Reflux; A solution of methyl 3-amino-2-hydroxybenzoate (1 g, 5.99 mmol) and p-toluenesulfonic acid (0.1 g, 0.581 mmol) in trimethylorthoformate (50 mL) was refluxed for 1 hour. Volatiles were evaporated under reduced pressure. The crude was purified by column chromatography on silica gel using 20:1 DCM:EtOAc as eluent to give methyl benzo[d]oxazole-7-carboxylate (0.99 g, 93%). UPLC-MS (Acidic Method, 2 min): rt 0.79 min, m/z 178.1 [M+H]+
 

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