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Chemical Structure| 371-14-2 Chemical Structure| 371-14-2

Structure of 371-14-2

Chemical Structure| 371-14-2

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Product Details of [ 371-14-2 ]

CAS No. :371-14-2
Formula : C6H7FN2
M.W : 126.13
SMILES Code : NNC1=CC=C(F)C=C1
MDL No. :MFCD00041262
InChI Key :ZXBMIRYQUFQQNX-UHFFFAOYSA-N
Pubchem ID :69982

Safety of [ 371-14-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H315-H318-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P403+P233-P405-P501
Class:8(6.1)
UN#:2922
Packing Group:

Application In Synthesis of [ 371-14-2 ]

* 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 [ 371-14-2 ]

[ 371-14-2 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 371-14-2 ]
  • [ 123-06-8 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
61% In ethanol; for 2h;Reflux; General procedure: A mixture of the appropriate phenylhydrazine (0.001 mol)and 10 mL of ethanol was stirred and allowed to reflux.Then, 2-(ethoxymethylene)malononitrile (0.001 mol) dissolvedin 10 mL of ethanol was slowly added. The reactionmixture was refluxed for 2 h. The reaction mixture waspoured into 50 mL of ice-cold water. The precipitate wascollected by filtration and washed with water to provide10a-c in 61-80% yield.5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile (10a)Yield: 61%. MP: 173-174 C. IR (cm-1): 3297-3183; 2225;1662; 1568; 1222. 1H NMR (400 MHz, DMSO-d6, TMS, deltain p.p.m.): 7.31-7.25; (m; 2 H; H3?, H5?); 7.54-7.49; (m;2H; H2?, H6?); 7.67; (s; 1 H; H3). 13C NMR (100 MHz,DMSO-d6, TMS, delta in ppm): 73.2 (C4); 114.8 (CN); 116.3(d; J = 22.8 Hz; C3?, C5?); 126.9 (d; J = 8.9 Hz; C2?, C6?);133.7 (d; J = 2.8 Hz; C1?) 141.7 (C5); 151.4 (C3); 161.2 (d;J = 243.6 Hz; C4?). 19F NMR (376 MHz, DMSO-d6, TMS, deltain p.p.m.): -114.26. EI [M + 1]+ 203.07.
61% In ethanol; for 2h;Reflux; General procedure: A mixture of the appropriate phenylhydrazine (0.001 mol) and10 mL of ethanol was stirred and allowed to reflux. Then, 2-(ethoxymethylene)malononitrile (0.001 mol) dissolved in 10 mL of ethanol was slowly added. The reaction mixture was refluxed for 2 h. The reaction mixture was poured into 50 mL of ice-cold water. The precipitate was collected by filtration and washed with water to produce 7-12 in 48-90% yield.
In ethanol; for 3h;Reflux; General procedure: A stirred mixture of para-substituted phenylhydrazine hydrochloride (0.025 mol) was dissolved inH2O (30 mL), then the pH of the mixture was adjusted to pH 7-8 by the dropwise addition of 10% NaOHsolution to form the free para-substituted phenyl hydrazines, which were then refluxed for 3 h withethoxymethylene malononitrile in an ethanol medium. After completion of the reaction, the reactionmixture was allowed to cool at room temperature, and the solid 2a-2d were filtered under vacuum. Thecrude products obtained were recrystallized from DMF to afford the pure products.
  • 2
  • [ 80370-42-9 ]
  • [ 371-14-2 ]
  • [ 138907-73-0 ]
  • 3
  • [ 25602-68-0 ]
  • [ 371-14-2 ]
  • [ 147213-06-7 ]
  • 4
  • [ 371-14-2 ]
  • [ 122-51-0 ]
  • [ 109-77-3 ]
  • [ 51516-70-2 ]
  • 5
  • [ 2689-69-2 ]
  • [ 371-14-2 ]
  • 3-(4-Fluor-phenylhydrazono)-tetrahydro-thiophen-2-carbonsaeure-methylester [ No CAS ]
  • 7
  • [ 371-14-2 ]
  • [ 146137-79-3 ]
  • C14H9F2N3 [ No CAS ]
  • 8
  • [ 6283-81-4 ]
  • [ 371-14-2 ]
  • [ 1215002-56-4 ]
  • 9
  • [ 68350-76-5 ]
  • [ 371-14-2 ]
  • [ 138907-68-3 ]
  • 10
  • [ 120-72-9 ]
  • [ 371-14-2 ]
  • [ 101125-32-0 ]
  • 11
  • [ 1118-61-2 ]
  • [ 371-14-2 ]
  • [ 76606-39-8 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride; In water; for 0.416667h;Heating; General procedure: To a solution of the corresponding arylhydrazine (1a-e) (10 mmol) in concentrated hydrochloric acid (5 mL), 820 mg of 3-aminocrotonitrile (2) (10 mmol) was added with magnetic stirring. The mixture was left to react for 10 minutes and then more HCl was added (5 mL) while heating for 15 additional minutes. After completion of the reaction, a yellow solution was obtained which was then cooled by addition of crushed ice and neutralized with concentrated ammonium hydroxide. Finally, the formed precipitate corresponding to aminopyrazoles 3a-e, was vacuum filtered and washed with cold water.
  • 12
  • [ 66495-88-3 ]
  • [ 371-14-2 ]
  • C14H13FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In ethanol; at 20℃; for 8h; General procedure: To a solution of aryl-aldehydes (5.0 mmol) and the corresponding phenylhydrazines (5.0 mmol)in ethanol (25 mL), was added one drop of acetic acid. The reaction mixture was stirred at roomtemperature for 8 h. After removing of the solvent, the residue was dissolved in CH2Cl2 (DCM) (20 mL),washed by water (10 mL), dried over Na2SO4, filtered and concentrated to give the hydrazones M2that were used without further purification.
  • 13
  • [ 3012-80-4 ]
  • [ 371-14-2 ]
  • (E)-2-((2-(4-fluorophenyl)hydrazono)methyl)-1-methyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.8% In methanol; at 20℃; for 2h; General procedure: The equimolar aldehyde 3a-3d (1 mmol) and substituted phenylhydrazine 5a-5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a-6ai (in 45-80% yield).
  • 14
  • [ 3314-30-5 ]
  • [ 371-14-2 ]
  • (E)-2-((2-(4-fluorophenyl)hydrazono)methyl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.8% In methanol; at 20℃; for 2h; General procedure: The equimolar aldehyde 3a?3d (1 mmol) and substituted phenylhydrazine 5a?5s (1 mmol) weremixed in CH3OH (10 mL) and stirred at room temperature [18]. After about 2 h, the reaction wascompleted (monitored by TLC). The residual crude was purified via silica gel column chromatogramusing a gradient mixture of petroleum ether and ethyl acetate to obtain the pure target compounds6a?6ai (in 45?80percent yield).
  • 15
  • [ 2469-99-0 ]
  • [ 371-14-2 ]
  • [ 76606-39-8 ]
YieldReaction ConditionsOperation in experiment
100% With acetic acid; In ethanol;Reflux; General procedure: A solution of (4-fluorophenyl)hydrazine (HCl salt, 802 mg, 5.8 mmol) and 3-oxo-butyronitrile (500 mg, 5.8 mmol) in EtOHIAcOH (10 mL/0.2 mL) was stirred at refluxing overnight. The reaction solution was concentrated in vacuum to give crode 2-(4-fluorophenyl)-5-methyl-2H-pyrazol-3-ylamine (1.1 g, yield:quantitative) as a yellow solid which was used for the next step without any purification. ‘H NMR (400 MHz,DMSO-d6): = 7.6-7.64 (m, 2H), 7.45 (t, J= 8.8 Hz, 1H), 5.66 (s, 1H), 2.24 (s, 3H).
  • 16
  • [ 763-33-7 ]
  • [ 371-14-2 ]
  • [ 76606-39-8 ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 16h;Reflux; General procedure: (E)-3-aminobut-2-enenitrile (2.3 g, 28 mmol) and (4-(trifluoromethyl)phenyl)hydrazine (5.0 g, 28 mmol) were taken EtOH (30 mL) heated to reflux for 16 hr. The mixture was cooled and poured into water (100 mL) and extracted with EtOAc (2x 100 mL). The organic phase was washed with brine, dried over MgSO4, filtered and then concentrated to yield 6.7 g (99% crude yield) of SI-1 as a dark red oil, which was used in the next step without further purification.
  • 17
  • [ 86240-43-9 ]
  • [ 371-14-2 ]
  • [ 51516-70-2 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 80℃; for 4h; General procedure: A round bottom flask were charged with P-substituted phenyl-hydrazine (1mmol) and 2-(ethoxymethyl) malononitrile/2-cyano-3-ethoxypropanoic acid (1.2mmol) in the ethanol and the mixture was heated to 80C and refluxed for 4h. After the reaction was completed, the mixture was vacuum filtered and concentrated to obtain intermediate 7.
 

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