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Chemical Structure| 77458-34-5 Chemical Structure| 77458-34-5

Structure of 77458-34-5

Chemical Structure| 77458-34-5

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Product Details of [ 77458-34-5 ]

CAS No. :77458-34-5
Formula : C10H10N2O
M.W : 174.20
SMILES Code : OC1=CN(C2=CC=C(C)C=C2)N=C1
English Name :1-(p-Tolyl)-1H-pyrazol-4-ol

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Application In Synthesis of [ 77458-34-5 ]

* 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 [ 77458-34-5 ]

[ 77458-34-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 337957-59-2 ]
  • [ 77458-34-5 ]
YieldReaction ConditionsOperation in experiment
91% With 3-chloro-benzenecarboperoxoic acid In chloroform at 60 - 70℃; for 2h; Step 1 General procedure: To a solution of 1,3-diphenylpyrazole-4-carboxaldehyde(1b, 10 g, 0.04mol) in chloroform (100mL) wasadded mCPBA (13.91 g, 0.08 mol) and the reaction mixturewas heated to 60-70 °C for 2 h. After completion of thereaction as followed by TLC, the reaction mixture was cooledto room temperature (RT) and washed with 10% Na2CO3solution (2×50mL) (to remove excess mCPBA). Theorganic layer was separated, dried over anhydrous sodiumsulphate and concentrated in vacuo to give 9.5 g of residue.
75 % Stage #1: 1-(p-tolyl)-1H-pyrazole-4-carbaldehyde With 3-chloro-benzenecarboperoxoic acid In chloroform Inert atmosphere; Reflux; Stage #2: With hydrogenchloride; methanol In water Reflux; 1.3 1-(p-tolyl)-1H-pyrazole-4-ol m-Chloroperbenzoic acid (8.34 g, 48.36 mmol, 0.9 equiv.) was added to a solution of 1- (p-tolyl ) -lff-pyrazole-4-carbaldehyde (10.0 g, 53.74 mmol, 1.0 equiv.) in chloroform (500 mL) at room temperature under nitrogen atmosphere. The resulting mixture was refluxed for 4h. The reaction mixture was then cooled to room temperature, diluted with DCM (100 mL) , washed with sodium bicarbonate solution (3 x 100 mL) followed by distilled water (3 x 100 mL) , dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product . Methanol (50 mL), distilled water (25 mL) , followed by concentrated HC1 (50 mL) was added to the crude product and then the reaction mixture was refluxed for lOh. After cooling to room temperature, all volatiles were distilled-off under reduced pressure . The pH of the reaction mixture was then made neutral by adding sodium bicarbonate solution and extracted with ethyl acetate (3 x 100 mL) . The combined organic layer was washed with distilled water , dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. The crude product thus obtained was purified by column chromatography on silica gel with a mixture of ethyl acetate and n-hexane as an eluent to afford 1- (p-tolyl ) -lJJ-pyrazol-4-ol as a light brown solid (7.0 g, Yield 75%) . (0452) NMR (CDC13) : 7.56 (s, 1H) , 7.46 (d, J= 8.4 Hz, 2H) , 7.41 (s, 1H) , 7.22 (d, J = 8.4 Hz, 2H) , 4.86 (bs, 1H) , 2.36 (s, 3H) ; MS (M+l) 175.13.
 

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