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Chemical Structure| 1521-41-1 Chemical Structure| 1521-41-1
Chemical Structure| 1521-41-1

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3,4-Dimethoxybenzamide is a natural product isolated and purified from the leaves of Litsea costalis (Nees) Kosterm..

Synonyms: 3,4-Dimethoxybenzamide

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Product Details of 3,4-Dimethoxybenzamide

CAS No. :1521-41-1
Formula : C9H11NO3
M.W : 181.19
SMILES Code : COC1=C(OC)C=C(C=C1)C(N)=O
Synonyms :
3,4-Dimethoxybenzamide
MDL No. :MFCD00017128
InChI Key :XNDZRGTVUVVHQT-UHFFFAOYSA-N
Pubchem ID :73705

Safety of 3,4-Dimethoxybenzamide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3,4-Dimethoxybenzamide

* 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 [ 1521-41-1 ]

[ 1521-41-1 ] Synthesis Path-Downstream   1~54

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  • [ 2757-23-5 ]
  • [ 67048-90-2 ]
  • 17
  • 2-benzoyl-3-(3,4-dimethoxy-phenyl)-3-oxo-propionic acid ethyl ester [ No CAS ]
  • ammonium hydroxide [ No CAS ]
  • [ 1521-41-1 ]
  • [ 55-21-0 ]
  • [ 4687-37-0 ]
  • [ 98-86-2 ]
  • 18
  • 3,4-Dimethoxy-benzaldehyde oxime [ No CAS ]
  • [ 2024-83-1 ]
  • [ 1521-41-1 ]
  • [ 33904-02-8 ]
  • 19
  • [ 120-14-9 ]
  • [ 2024-83-1 ]
  • [ 1521-41-1 ]
  • [ 33904-02-8 ]
  • 20
  • 3,4-Dimethoxy-benzaldehyde oxime [ No CAS ]
  • [ 1521-41-1 ]
YieldReaction ConditionsOperation in experiment
92% With [(eta.(5)-pentamethylcyclopentadienyl)Ir(H2O)3](OTf)2; In water; at 110℃; for 12h;Schlenk technique; To a stirred solution of 3, 4-dimethoxybenzaldehyde oxime (90.6 mg, 0.5 mmol), [Cp * Ir (H20) 3] [0Tf] 2 (5.1 mg, 0.0075 mmol, %) And water (lml) were added sequentially to a 25 ml Schlenk reaction flask. The reaction mixture was allowed to react at 110 C for 12 hours, then cooled to room temperature. The water was removed by rotary evaporation, and the product was isolated by column chromatography. Yield: 92%. (D, J = 1.9Hz, 2H, ArH), 7.34 (dd, J = 8.3Hz and J = 1.9Hz, 1Hz, ArH). NMR (500MHz, CDC13) , 3.88 (d, J = 8.4Hz, 1 H, ArH), 6.00 (br s, 1 H, N H), 5.88 (br s, 1 H, 13C NMR (125 MHz, CDC13)? 169.2, 152.1, 148.9, 125.8, 120.1, 110.7, 110. 2, 3? 56. 0.
82% With [(eta.(5)-pentamethylcyclopentadienyl)Ir(H2O)3](OTf)2; water; at 110℃; for 12h;Schlenk technique; A mixture of 3,4-dimethoxybenzaldehyde oxime(83.1 mg, 0.5 mmol),[Cp * Ir (H2O) 3] [OTf] 2 (10.2 mg, 0.0150 mmol, 3 mol%)And water (1 ml) were sequentially added to a 25 ml Schlenk reaction flask.The reaction mixture was allowed to react at 110 C for 12 hours,Cooled to room temperature,Rotary evaporation to remove water,Column to give the title compound,Yield: 82%.
82.9% With 732-type strongly acidic cation exchange resin; In toluene; for 0.5h;Reflux; In a container adding veratraldehyde 1.66g, hydroxylamine hydrochloride 0.95g and water 20 ml, heating to 40 C, stirring 30min; room temperature, for 40% aqueous sodium hydroxide solution to adjust the pH=7, filtering, washing, drying, to obtain the eater aldoxime; added in to the container by the radix of the aldoxime, activation of the 732-type strongly acidic cation exchange resin 30g and toluene 40 ml, heating to reflux, the reaction 0.5h; the temperature to room temperature, filter, recovery ion exchange resin, the filtrate is concentrated; the crude product in ethyl acetate/hexane recrystallization, get the compound goal white solid veratridine amide 1.50g, yield is 82.9%.
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  • [ 630-19-3 ]
  • [ 1158074-47-5 ]
  • 34
  • 3-tosyloxyacetyl-1'-benzenesulfonylindole [ No CAS ]
  • [ 1521-41-1 ]
  • [ 1220958-34-8 ]
  • 35
  • [ 120-14-9 ]
  • [ 1521-41-1 ]
YieldReaction ConditionsOperation in experiment
75% With hydroxylamine hydrochloride; C59H50ClN2OP2Ru; sodium hydrogencarbonate; In acetonitrile; for 5h;Inert atmosphere; Reflux; General procedure: The reaction vessel was equipped with magnetic stirring bar, complex catalyst(1 mol%), aldehyde (1 mmol), NH2OHHCl(1 mmol) and NaHCO3 (1 mmol) was taken and the mixture was placed under an atmosphere of N2. Dry and degassed acetonitrile(3 mL) was added and the reaction mixture was refluxed for 5 h.The reaction mixture was then cooled to room temperature and the solvent was evaporated. The residue was dissolved in CH2Cl2,filtered and the solvent was removed. The amide was then purified using column chromatography, which gives the amide in high isolated yield. The products were confirmed by1H NMR spectra.
  • 36
  • [ 93-03-8 ]
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  • 1,3-bis-(3,4-dimethoxyphenyl)urea [ No CAS ]
  • 37
  • [ 91-16-7 ]
  • [ 75-52-5 ]
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  • 39
  • 3,4-Dimethoxy-benzaldehyde oxime [ No CAS ]
  • [ 2024-83-1 ]
  • [ 1521-41-1 ]
  • 40
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  • [ 501-65-5 ]
  • [ 1404499-96-2 ]
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  • 44
  • [ 141-32-2 ]
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  • butyl (Z)-2-(5,6-dimethoxy-3-oxoisoindolin-1-ylidene)acetate [ No CAS ]
  • 45
  • [ 5888-51-7 ]
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YieldReaction ConditionsOperation in experiment
81% With tert.-butylhydroperoxide; ammonia; iodine; In water; at 100℃; for 3h;Sealed tube; Green chemistry; General procedure: A sealed tube equipped with a magnetic stirring bar was charged with ethylarene (1, 1.0 mmol), aq NH3 (2, 25% aq solution,10.0 mmol), I2 (1.1 mmol), and TBHP (6.0 mmol, 70% aq solution) at r.t. The resulting mixture was heated to 100 C for 3.0 h. After completion of the reaction (monitored by TLC), sat.Na2S2O3 solution (10 mL) was added to the reaction mixture,and it was extracted with EtOAc (2 × 20 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on 100-200 mesh silica gel using EtOAc-n-hexane (1:2) as the eluent to obtain the corresponding benzamide 3.
  • 46
  • [ 61117-58-6 ]
  • [ 2859-78-1 ]
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YieldReaction ConditionsOperation in experiment
87% With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 90℃; for 3h;Sealed tube; General procedure: To a stirred solution of aryl halide (Br/I) (1 mmol) in dry dioxane in a 25 mL sealed tube, was added Pd(OAc)2 (5 mol%), dppf (6 mol %), DIPEA (2 mmol), imidazole (0.25 mmol), ammonium chloride (2 mmol) and then Co2(CO)8 (0.3 mmol). The seal tube was closed immediately and stirred at 90 C for 3h. After the reaction time the reaction mixture was cooled to room temperature. The reaction mixture was filtered through celite pad and washed with dioxane, the filtrate was concentrated under reduced pressure and the residue obtained was purified by column chromatography.
  • 47
  • [ 93-07-2 ]
  • [ 2024-83-1 ]
  • [ 1521-41-1 ]
YieldReaction ConditionsOperation in experiment
67%; 30% With diisobutylaluminium hydride; ammonium chloride; In tetrahydrofuran; at 66℃; for 16h;Inert atmosphere; General procedure: The solution of aminoalane reagent (prepared from 20 equiv. DIBAL-H in case of ester and lactonesubstrates or from 40 equiv. in case of carboxylic acid and amide substrates) was added to a solutionof carboxylic acid (1 eqiuv.) or its derivative (lactone, ester or amide, 1 equiv.) in anhydrous THF atroom temperature. Stirring was continued for 16 hours at 66 C. After this time, the reaction mixturewas cooled, quenched with aqueous solution of KHSO4 and the product was extracted with CHCl3.The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified by silica gel chromatography with hexane / ethyl acetateelution.
  • 48
  • [ 3943-77-9 ]
  • [ 2024-83-1 ]
  • [ 1521-41-1 ]
YieldReaction ConditionsOperation in experiment
77%; 23% With diisobutylaluminium hydride; ammonium chloride; In tetrahydrofuran; at 66℃; for 16h;Inert atmosphere; General procedure: The solution of aminoalane reagent (prepared from 20 equiv. DIBAL-H in case of ester and lactonesubstrates or from 40 equiv. in case of carboxylic acid and amide substrates) was added to a solutionof carboxylic acid (1 eqiuv.) or its derivative (lactone, ester or amide, 1 equiv.) in anhydrous THF atroom temperature. Stirring was continued for 16 hours at 66 C. After this time, the reaction mixturewas cooled, quenched with aqueous solution of KHSO4 and the product was extracted with CHCl3.The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified by silica gel chromatography with hexane / ethyl acetateelution.
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  • [ 120329-58-0 ]
  • [ 1041381-45-6 ]
  • 52
  • [ 127-19-5 ]
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  • methylene bis(3,4-dimethoxybenzamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With sodium persulfate; ammonium cerium (IV) nitrate; In water; at 110℃; for 12h;Schlenk technique; Sealed tube; In a Schlenk tube charged successively 3,4-dimethoxy benzamide (0.5mmol), sodium persulfate (2mmol), ceric ammonium nitrate (0.025mmol), N, N- dimethylacetamide (2 mmol), 1ml of deionized water was added, the system was then sealed and heated in an oil bath at 110 deg.] C after about 12 hours. after completion of the reaction was cooled and extracted with ethyl acetate (15ml × 3), and concentrated by a simple column chromatography ( eluent petroleum ether: ethyl acetate = 2: 1) to giveMethylene-bis-3,4-dimethoxy-benzamide, the yield was 75%
  • 53
  • [ 1521-41-1 ]
  • 2-(3,4-dimethoxyphenyl)quinolin-4(1H)-one [ No CAS ]
  • 54
  • [ 1521-41-1 ]
  • 2-(3, 4-dimethoxyphenyl)-4-phenoxyquinoline [ No CAS ]
 

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