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Product Details of [ 3290-99-1 ]

CAS No. :3290-99-1 MDL No. :MFCD00017073
Formula : C8H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :REKQLYUAUXYJSZ-UHFFFAOYSA-N
M.W : 166.18 Pubchem ID :76792
Synonyms :

Calculated chemistry of [ 3290-99-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.83
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 0.25
Log Po/w (WLOGP) : 0.3
Log Po/w (MLOGP) : 0.88
Log Po/w (SILICOS-IT) : 0.19
Consensus Log Po/w : 0.61

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.2
Solubility : 10.5 mg/ml ; 0.0631 mol/l
Class : Very soluble
Log S (Ali) : -1.16
Solubility : 11.4 mg/ml ; 0.0689 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.16
Solubility : 1.15 mg/ml ; 0.00695 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.08

Safety of [ 3290-99-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3290-99-1 ]

* 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.

  • Upstream synthesis route of [ 3290-99-1 ]
  • Downstream synthetic route of [ 3290-99-1 ]

[ 3290-99-1 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 3290-99-1 ]
  • [ 122-51-0 ]
  • [ 829-35-6 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium chloride In ethanol for 0.5 h; Reflux General procedure: To asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.
92% at 100 - 110℃; for 12 h; To a mixture of 3 (18.0 g, 0.1083 mol) and triethyl orthoformate (80.3 g, 0.541 mol) was heated to 100-110 °C and maintained for 12 h. The reaction completion was monitored by TLC. The reaction mixture was cooled to room temperature and concentrated to syrup. Traces triethyl orthoformate was removed by azeotropic distillation with toluene. The residue was purified by column chromatography on silica gel using eluent 0-5percent ethyl acetate in petroleum ether. The title compound was yielded as pale yellow liquid (Yield: 17.55 g, 92percent).
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[4] Journal of the American Chemical Society, 2016, vol. 138, # 38, p. 12605 - 12614
[5] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 276 - 283
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[7] Journal of Organic Chemistry, 2009, vol. 74, # 16, p. 6410 - 6413
[8] Chemistry - A European Journal, 2011, vol. 17, # 30, p. 8294 - 8298
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[10] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2027,2030; engl. Ausg. S. 1996, 1998
[11] Organic Letters, 2010, vol. 12, # 15, p. 3567 - 3569
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[15] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11307 - 11309,3
[16] Tetrahedron, 2013, vol. 69, # 9, p. 2220 - 2225
  • 2
  • [ 3290-99-1 ]
  • [ 829-35-6 ]
YieldReaction ConditionsOperation in experiment
67% With trifluoroacetic acid In toluene at 130℃; for 12 h; General procedure: A 25 mL pressure tube was charged with arylhydrazide 1 (0.5 mmol), TFBen (53 mg, 0.25 mmol, white solid, mp 57.2-58.5 °C), TFA (38 μL, 1.0 equiv), and toluene (4 mL). The tube was then heated by stirring the contents at 130 °C for 12 h. Afterwards, the mixture was cooled to r.t., quenched with sat. aq NaHCO3 (3 mL), and extracted with EtOAc (3 4 mL). The combined organic layers were dried (anhyd Na2SO4), filtered, and concentrated under reduced pressure. The pure product 2 was obtained after purification by column chromatography (EtOAc/ pentane 1:3).
Reference: [1] Synthesis (Germany), 2018, vol. 50, # 16, p. 3238 - 3242
  • 3
  • [ 3290-99-1 ]
  • [ 149-73-5 ]
  • [ 829-35-6 ]
YieldReaction ConditionsOperation in experiment
96% With Al3+-K10 montmorillonite clay In neat (no solvent) at 55℃; for 0.25 h; Microwave irradiation General procedure: A 5 mL microwave vial was charged with acidhydrazide (100 mg, 1 eq), trimethyl orthoester (2 eq) and Al3+-K10 clay (75 mg). The resulting mixture was kept under microwave irradiation maintaining the temperature at 55 °C for 15 min (Microwave irradiations were performed on CEM-discover model No. 908010). The reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with ethyl acetate stirred well, filtered, washed well with ethyl acetate. Filtrate was evaporated under reduced pressure to obtain highly pure product. In some cases, products were purified by column chromatography using 60-120 mesh silica with 20-100 percent ethyl acetate in pet ether as eluting solvents. The catalyst recovered by filtration was reused for another 5 more times.
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  • 4
  • [ 3290-99-1 ]
  • [ 100-06-1 ]
  • [ 829-35-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 12, p. 2960 - 2963
  • 5
  • [ 3290-99-1 ]
  • [ 536-74-3 ]
  • [ 829-35-6 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6820 - 6825
  • 6
  • [ 292638-84-7 ]
  • [ 3290-99-1 ]
  • [ 829-35-6 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 15, p. 6820 - 6825
  • 7
  • [ 2290-65-5 ]
  • [ 3290-99-1 ]
  • [ 1014-25-1 ]
Reference: [1] RSC Advances, 2013, vol. 3, # 19, p. 6813 - 6816
  • 8
  • [ 3290-99-1 ]
  • [ 1014-25-1 ]
Reference: [1] Arkivoc, 2017, vol. 2017, # 5, p. 293 - 300
  • 9
  • [ 121-98-2 ]
  • [ 3290-99-1 ]
YieldReaction ConditionsOperation in experiment
96% With hydrazine hydrate In ethanol for 6 h; Reflux 4-Methoxybenzohydrazide was synthesized according to the literature[22]. A mixture of methylmethoxybenzoate (1.66 g, 0.01 mol) andhydrazine hydrate (3.6 ml, 0.06 mol) in ethanol (20 mL) was heatedunder reflux for 6 h. The solvent was removed and the precipitate wasobtained. The solid product was recrystallized with ethanol to give 4-methoxybenzohydrazide as colorless crystals. Yield 96percent, mp 138–139 °C.
90% With hydrazine In methanol; water at 45℃; for 24 h; Example I 4-methoxy-benzoic acid hydrazide A solution of methyl 4-methoxybenzoate, (5.0 g, 0.03 mol) in methanol (20 mL) was treated with hydrazine hydrate (12.0 g, 0.24 mol) and the mixture stirred at 45° C. for 24 hours. The reaction mixture was concentrated and the residue partitioned between EtOAc (50 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (3.x.20 mL), and the combined organic extracts washed with brine (20 mL), dried over Na2SO4, and concentrated to give the desired hydrazide (compound 2) as solid which was crystallized by EtOAc giving white solid 4.50 g in 90percent yield, mp: 134.3° C. (Aldrich, mp: 136-140° C.). 1H NMR (CDCl3) δ 7.73 (d, 2H), 7.38 (s, 1H), 6.94 (d, 2H), 3.85 (s, 3H), 1.69 (s, 2H). 13C NMR (CDCl3) δ 165.5, 159.6, 125.7, 122.0, 111.1, 52.5. Anal. Calcd for C8H10N2O2.1/2H2O: C, 54.84; H, 5.75; N, 15.99. Found: C, 54.57; H, 5.59; N, 15.53.
88% for 4 h; Reflux In the 500 ml round bottom flask is added 53.15g (0.32 µM) 4 - methoxybenzoic acid methyl ester, 300ml50percent hydrazine hydrate reflux 4h, changing device, for the majority of the solvent water pump by reducing pressure, the residual liquid is separated out light yellow crystal after cooling, filtering, drying, and for using ethanol to recrystallize the decolorize with active carbon, to obtain white crystal, yield 88percent
87% With hydrazine hydrate In ethanolReflux General procedure: To a solution of the appropriate methyl benzoate ester (1.0 mmol) in ethanol (30 mL), hydrazine monohydrate (0.15 g, 3.0 mmol) was added. The reaction mixture was heated under reflux overnight. After completion of the reaction, the solvent was evaporated under reduced pressure, and the residue was washed with water (2 x 3 mL), and the obtained solid was filtered and dried to give benzohydrazide derivatives 3a-c.
85% With hydrazine hydrate In methanol for 5 h; Reflux General procedure: To a solution of an appropriate methyl esters17(a–j) (1.0 mmol) in 50 mL of methanol was added 99 percenthydrazine hydrate (4.0 mmol) and the mixture was refluxedfor 5 h up to reaction completed (TLC). After completionof reaction, it was allowed to cool and the obtained solidwas washed with methanol. The crude products wererecrystallized from ethanol.
70% With hydrazine hydrate In ethanol for 5 h; Reflux General procedure: A solution of hydrazine hydrate (20.00 mmol) in 2 mL EtOH was added dropwise to the ester 2 (5.00 mmol). The mixture was refluxed for 5 h and filtered, and the corresponding acid hydrazide 3 was obtained by washing the residue with ice water.
69% With hydrazine hydrate In ethanol for 5 h; Reflux General procedure: Compound 12 (0.013 mol) and 80percent NH2NH2H2O (5 mL) wereadded to EtOH (10 mL), the mixturewas stirred under reflux for 5 h.After being cooled to room temperature, the precipitate was obtainedby filtration, and was dried to give the title compounds,respectively.

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  • 10
  • [ 94-30-4 ]
  • [ 3290-99-1 ]
YieldReaction ConditionsOperation in experiment
89% With hydrazine hydrate In ethanol; waterReflux General procedure: Hydrazides (30–58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3–6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
88% With hydrazine hydrate In ethanolReflux General procedure: Ethylbenzoates (11-15, 1.5g, 9.98 mmol)and ethyl-2-phenylacetates (16-20, 1.5g, 9.13 mmol)were dissolved in ethanol and then hydrazine-hydrate(99percent) was added and reux for 8-12h. Ethanol wasconcentrated and the resultant residue was pouredin ice cold water and stirred for 15 -20 min, the solidsthat were thrown out was fltered at the pump anddried to obtain the corresponding benzohydrazides(21-25) and 2-phenylacetohydrazides (26-30) in 80-82percent yield.
80% With hydrazine hydrate In ethanol at 0℃; for 3 h; To a mixture of 2 (25.0 g, 0.1387 mol) in ethanol (200mL) at 0-5 °C, hydrazine hydrate (13.87 mL, 0.2774 mol) was added. The reaction mass was heated to reflux for 2.0 h. The reaction completion was monitored by TLC. The reactionmixture was cooled to 0-5 °C stirred for 60 min. The solid formed was filtered and dried to get compound 3 as white solid (Yield: 18.4 g, 80percent).
80.2% With hydrazine hydrate In ethanolReflux General procedure: A solution of the isolated esters 2a–e (10mmol) in ethanol (20mL), hydrazine hydrate (97percent, 3mL) was added and heated under reflux for 5–8h. After cooling, the formed precipitate was filtered off, washed with water, dried, and crystallized from ethanol.
80.2% With hydrazine hydrate In ethanolReflux General procedure: Hydrazine hydrate (97percent, 30 mmol, 1.5 mL) was added to a solutionof the isolated esters 2a–e (10 mmol) in ethanol (20 mL), and themixture was heated at reflux for 5–8 h. After cooling, the resultingprecipitate was filtered off, washed with water, dried, and crystallizedfrom ethanol.
70% With hydrazine hydrate In ethanol for 12 h; Reflux; Inert atmosphere; Schlenk technique General procedure: Hydrazine monohydrate (5 mmol) was added dropwise to a solution of compounds 1A-C (1mmol) in EtOH. The mixture was refluxed for 12 h, and then the solvent was removed by rotary evaporation. The residue was treated with water and extracted with CH2Cl2. The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by rotary evaporation. The residue was purified by recrystallization.

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[66] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5652 - 5661
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  • 11
  • [ 100-09-4 ]
  • [ 3290-99-1 ]
YieldReaction ConditionsOperation in experiment
87% at 250℃; Microwave irradiation General procedure: Acyl hydrazides were synthesized in excellent yields from thereaction of substituted aryl acids (0.010 mol) with hydrazine hydrate(0.012 mol) in absence of organic solvents under microwaveirradiation (300 W, 250 C) for 4e8 min. Spectral analysis of thesynthesized hydrazides are consistent with the proposed structuresand with those reported [58].
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  • 12
  • [ 100-07-2 ]
  • [ 3290-99-1 ]
YieldReaction ConditionsOperation in experiment
84% With hydrazine hydrate; triethylamine In acetonitrile for 3 h; Compound 1b is prepared by reacting compound 1a (1 mmol), 1,2-dichloroethane (DEC) (12 mL) and chlorinating agent (0.4 mL) while refluxing for 3 hours. Then, the obtained solution was cooled at room temperature After removal of the solvent under reduced pressure, compound 1b is obtained, which is subjected to the next step without further purification . The compound Compound 1b was dissolved in acetonitrile (80 mL), and hydrazine hydrate (1 mmol), Was added dropwise to a solution containing TEA (0.5 mL) and acetonitrile (20 mL), which was monitored by TLC, Respectively. After the reactants were exhausted, the reaction mixture was cooled to room temperature. Subsequently, the solvent was evaporated under reduced pressure to give To give crude 4-methoxybenzohydrazide (Compound 1c) as a white solid, which was purified by column chromatography Purification by column chromatography and crystallization in methanol gives the product (Compound 1c).
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[8] Journal of Molecular Structure, 2017, vol. 1138, p. 177 - 191
  • 13
  • [ 3424-93-9 ]
  • [ 3290-99-1 ]
YieldReaction ConditionsOperation in experiment
87% With silica gel; hydrazine In neat (no solvent) at 130℃; for 20 h; Inert atmosphere; Sealed tube General procedure: These compounds were prepared using the standard procedure at 130°C for 20–24h. For each reaction, the crude product was adsorbed onto silica gel and purified on a 15cm×2.5cm silica gel column eluted with 80percent EtOAc in hexanes. The isolated yields are given in Table 7.
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