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Chemical Structure| 1012879-55-8 Chemical Structure| 1012879-55-8

Structure of 1012879-55-8

Chemical Structure| 1012879-55-8

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Product Details of [ 1012879-55-8 ]

CAS No. :1012879-55-8
Formula : C22H17N3
M.W : 323.39
SMILES Code : C12=CC(NN=C(C3=CC=CC=C3)C4=CC=CC=C4)=CC=C1N=CC=C2

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Application In Synthesis of [ 1012879-55-8 ]

* 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 [ 1012879-55-8 ]

[ 1012879-55-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1012879-55-8 ]
  • [ 13395-36-3 ]
  • [ 1020173-68-5 ]
YieldReaction ConditionsOperation in experiment
40 g With hydrogenchloride; In ethanol; at 80℃; A solution of N-benzhydrylidene-N'-quinolin-6-yl-hydrazine (32 g, 0.099 mol) in EtOH (500 mL) was treated with cone. HC1 (80 ml, 0.96 mmol). After stirring for 10 min, <strong>[13395-36-3]5,5-dimethyl-2,4-dioxo-hexanoic acid ethyl ester</strong> (26 g, 0.15 mol) was added, and the mixture was heated to 80C overnight. The reaction was concentrated in vacuo to give a residue which was washed with Et20 to afford ethyl 5- tert-butyl-l-(quinolin-6-yl)-lH-pyrazole-3-carboxylate hydrochloride (40 g, 0.1 1 mol, 1 12 % yield). MS (ESI) m/z: 324.1 (M+H+).
  • 2
  • [ 1012879-55-8 ]
  • [ 13395-36-3 ]
  • [ 1020173-69-6 ]
YieldReaction ConditionsOperation in experiment
A solution of N-benzhydrylidene-N'-quinolin-6-yl-hydrazine (32 g, 0.099 mol) in EtOH (500 mL) was treated with conc. HCl (80 ml, 0.96 mmol). After stirring for 10 min, <strong>[13395-36-3]5,5-dimethyl-2,4-dioxo-hexanoic acid ethyl ester</strong> (26 g, 0.15 mol) was added, and the mixture was heated to 80 C. overnight. The reaction was concentrated in vacuo to give a residue which was washed with Et2O to afford ethyl 5-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-3-carboxylate hydrochloride (40 g, 0.11 mol, 112% yield). MS (ESI) m/z: 324.1 (M+H+). A suspension of ethyl 5-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-3-carboxylate hydrochloride (32 g, 0.089 mol) in THF (300 mL) was treated with aqueous LiOH (2 N, 100 mL, 0.20 mmol) and the resultant mixture was heated to 40 C. for 3 hours. The reaction was concentrated under reduced pressure and the remaining aqueous layer was washed with EtOAc. The aqueous phase was acidified to pH 3 and the resultant precipitate was collected by filtration, washed with cold ether and dried in vacuo to provide 5-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-3-carboxylic acid (21 g, 71% yield). 1H-NMR (400 MHz, DMSO-d6) delta 9.03 (m, 1H), 8.50 (d, J=8.7 Hz, 1H), 8.20 (d, J=2.4 Hz, 1H), 8.15 (d, J=8.8 Hz, 1H), 7.79 (dd, J=8.7 Hz, 2.4 Hz, 1H), 7.67 (dd, J=8.4, 4.4 Hz, 1H), 6.68 (s, 1H), 1.17 (s, 9H); MS (ESI) m/z: 296.3 (M+H+).
 

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