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Chemical Structure| 771-28-8 Chemical Structure| 771-28-8

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Chemical Structure| 771-28-8

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Product Details of [ 771-28-8 ]

CAS No. :771-28-8
Formula : C8H10N2O2
M.W : 166.18
SMILES Code : N=C(NO)C1=CC=CC=C1OC
MDL No. :MFCD06366748

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Application In Synthesis of [ 771-28-8 ]

* 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 [ 771-28-8 ]

[ 771-28-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6609-56-9 ]
  • [ 771-28-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydroxylamine; In ethanol; water; at 20 - 55℃; for 40h; Hydroxylamine (Fluka 55458; 50% in water; 11.28 ml 187.76 mmol; 5 eq.) was added to a solution of 2-methoxybenzonitrile (Alrich 231231 ; 4.59 ml 37.55 mmol; 1 eq.) in EtOH (50 ml_) and the resulting mixture was stirred at room temperature for 16 hours then at 55C for 24 hours. The solvent was then evaporated and the resulting colourless oil was further dried under high vaccum to give a white solid. The latter was triturated in n-hexane, filtered and dried to afford the title compound (6.29 g, quantitative) as a white solid. HPLC (Method A) : Rt 0.96 min (purity 99.2%).
73% With hydroxylamine hydrochloride; sodium hydrogencarbonate; In ethanol; for 6h;Reflux; General procedure: To a stirred suspension of nitrile (30 mmol) and hydroxylaminehydrochloride (3.13 g, 45 mmol) in EtOH (50 mL) a NaHCO3 (3.78 g,45 mmol)was added. The reaction mixturewas stirred under refluxfor 6 h. After the reaction had completed, the reaction mixture wasconcentrated under reduced pressure, and the residue was dilutedwith cold water (80 mL). The resulting precipitate was filtered off,washed with cold water (20 mL) and dried in air at roomtemperature.
63% With hydroxylamine hydrochloride; potassium carbonate; In methanol; for 6h;Reflux; General procedure: A 1.3 g of a solution of 4-chorobenzonitrile (16v, 9.69 mmol, 1 equivalent) was dissolved in 50 mL of methanol. To this 2 g of K2CO3 (14.53 mmol, 1.5 equiv) was added and mixed properly. The reaction mixture was cooled at 0 C, and 1.35 g of hydroxylamine hydrochloride (19.38 mmol, 2 equiv) was added in portion-wise. After completion of the addition, it was refluxed for 6 hr.Then evaporated the solvent and excess of water was added to afford the precipitate of the desired product which was filtered and dried.
50% With hydroxylamine hydrochloride; sodium carbonate; In water; at 20℃; General procedure: Na2CO3 (3.61 g, 34 mmol) was dissolved in water (83 mL), and NH2OHxHCl (4.30 g, 61.4 mmol) was slowly added. After complete removing of CO2 appropriate nitrile (19 mmol) was added and mixture was stirred at room temperature for several days. Solvents were evaporated under reduced pressure to final volume of 50 mL. Obtained solution was extracted with ethylacetate (2 x 50 mL) and dried over Na2SO4. The solvent was removed at reduced pressure, to give the raw product that was finally purified by crystallization in ethyl acetate or by chromatography on SiO2, eluting with hexane/ethyl acetate (yields 20-50 %).

  • 2
  • [ 6609-56-9 ]
  • [ 771-28-8 ]
YieldReaction ConditionsOperation in experiment
91% With potassium hydroxide; hydroxyamino hydrochloride; In ethanol; at 20℃; for 12h;Heating / reflux; Add potassium hydroxide (30.3 g, 225 mmol) to a solution of 2- methoxybenzonitrile (25.0 g, 187 mmol) and hydroxylamine hydrochloride (15.77 g, 225 mmol) in ethanol (500 mL) at room temperature under nitrogen and heat the mixture at reflux for 12 hours. Remove the solvent under reduced pressure, triturate the residue with ethyl acetate/hexanes (1: 9,300 mL) and collect by vacuum filtration to provide N hydroxy-2-methoxybenzamidine (24.0 g, 91%).
With hydroxyamino hydrochloride; Sodium hydrogenocarbonate; In methanol; at 20 - 80℃; for 48h; General procedure: General Method A for the synthesis of hydroxyamidines (A-4)To a solution of nitrile-derivative (1.0 eq.) in MeOH (0.5 M), hydroxylamine HCI (1.1 to 3.0 eq.)and NaHCO3 (1.1 to 3.0 eq.) was added at rt. The resulting suspension was stirred at a giventemperature and time (see Table 5). The mixture was concentrated in vacuo, then EtOAc wasadded to the remaining residue and the org. layer was washed with brine (lx), dried (MgSO4), filtered and concentrated to yield hydroxyamidine A-4. Listed in Table 5 below are hydroxylamidines of type A-4, prepared from either commercially available nitrile-derivates or synthesized according to described methods.
2.8 g With hydroxyamino hydrochloride; triethylamine; In ethanol; lithium hydroxide monohydrate; at 70℃; for 15h; To a stirred solution of 2-methoxybenzonitrile (2.0 g, 15.0 mmol, 1 .83 mL) in ethanol (20 mL) were added hydroxylamine hydrochloride (2.09 g, 30.0 mmol), triethylamine (3.04 g, 30.0 mmol, 4.16 mL), and water (2 mL), then the mixture was heated to 70 00 for 1 5h. The mixture was cooled and quenched with water (20 mL), extracted with dichloromethane (30 mL x 3), and the combined organicphases were washed with water (20 mL), saturated aqueous sodium chloride solution (20 mL), dried overanhydrous sodium sulfate, filtered, and concentrated to give N-hydroxy-2-methoxybenzimidamide (2.80 g)as a light green solid, which was used in next step directly. 1H NMR (400 MHz, Methanol-d4) O 7.47 -7.30 (m, 2H), 7.06 (d, J8.4 Hz, 1H), 6.95 (t, J7.5 Hz, 1H), 3.86 (s, 3H).
 

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