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[ CAS No. 3400-22-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3400-22-4
Chemical Structure| 3400-22-4
Chemical Structure| 3400-22-4
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Product Details of [ 3400-22-4 ]

CAS No. :3400-22-4 MDL No. :MFCD00522600
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SIOAPROKUUGJAQ-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :346031
Synonyms :

Calculated chemistry of [ 3400-22-4 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.93
TPSA : 38.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.91
Log Po/w (XLOGP3) : 1.0
Log Po/w (WLOGP) : 1.05
Log Po/w (MLOGP) : 1.23
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.67
Solubility : 3.56 mg/ml ; 0.0216 mol/l
Class : Very soluble
Log S (Ali) : -1.39
Solubility : 6.67 mg/ml ; 0.0404 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.206 mg/ml ; 0.00125 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 3400-22-4 ]

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

Application In Synthesis of [ 3400-22-4 ]

* 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 [ 3400-22-4 ]

[ 3400-22-4 ] Synthesis Path-Downstream   1~89

  • 1
  • [ 100-07-2 ]
  • [ 74-89-5 ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; water; at 0 - 20℃; for 1h; General procedure: Triethylamine (15 mmol), 33.3% methylamine in water (20 mmol) were added tothe solution of acid chloride (10 mmol) in CH2Cl2 (20 mL) at 0C. The reactionmixture was stirred at room temperature for 1 h and monitored by TLC until thereaction was completed. Then water (50 mL) was added to the mixture and extractedwith CH2Cl2 (30 mL). The organic phase was dried over anhydrous Na2SO4 andconcentrated under reduced pressure. The residue can be purified by silica gel flashchromatography or recrystallization, and the corresponding benzamide products canbe obtained with a yield of 80-95%.
  • 2
  • [ 696-63-9 ]
  • [ 201230-82-2 ]
  • [ 622-29-7 ]
  • [ 98098-60-3 ]
  • [ 68162-88-9 ]
  • [ 3400-22-4 ]
  • 3
  • [ 13214-64-7 ]
  • [ 3400-22-4 ]
  • 4
  • [ 5335-05-7 ]
  • [ 3400-22-4 ]
  • [ 134814-88-3 ]
  • 5
  • [ 3400-22-4 ]
  • [ 132606-41-8 ]
  • 6
  • [ 3400-22-4 ]
  • [ 78554-86-6 ]
YieldReaction ConditionsOperation in experiment
11.9 g (76%) With thionyl chloride; EXAMPLE I N-Methyl 4-Methoxybenzimidoyl Chloride N-Methyl 4-methoxybenzamide (13.95 g, 84.5 mmole) was placed in a 50 ml round bottom flask equipped with magnetic stirrer, heating mantle, condenser and base trap. Thionyl chloride (33 g, 278 mmole) was added. The reaction was stirred and heated at reflux until gas evolution ceased (three hours). The excess thionyl chloride was distilled at ca. 15 mm Hg, and the product distilled at 75-80 C. (0.1 mm Hg) to yield 11.9 g (76%) of the title compound as a clear colorless liquid.
  • 7
  • [ 3400-22-4 ]
  • [ 100-09-4 ]
  • 8
  • [ 84-51-5 ]
  • [ 3400-22-4 ]
  • C32H24O6 [ No CAS ]
  • 9
  • [ 86-81-7 ]
  • [ 3400-22-4 ]
  • [ 212501-06-9 ]
  • 10
  • [ 2186-24-5 ]
  • [ 3400-22-4 ]
  • 2-(2-hydroxy-3-<i>p</i>-tolyloxy-propyl)-4-methoxy-<i>N</i>-methyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-methoxy-N-methylbenzamide With n-butyllithium In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Stage #2: cresyl-glicidyl ether In tetrahydrofuran; diethyl ether at -15 - 20℃;
  • 11
  • [ 93-89-0 ]
  • [ 3400-22-4 ]
  • [ 919475-63-1 ]
  • 12
  • [ 3400-22-4 ]
  • 2-{3-hydroxy-2-[(pyridin-3-ylmethyl)amino]propyl}-6-methoxy-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbonitrile [ No CAS ]
  • 13
  • [ 3400-22-4 ]
  • 2-(2-amino-3-diphenylsilanyloxy-propyl)-6-methoxy-1-oxo-4-phenyl-1,2-dihydro-isoquinoline-3-carbonitrile [ No CAS ]
  • 14
  • [ 100-07-2 ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
a. 4-Methoxy-N-methylbenzamide. Using a procedure similar to that described in Example 28 sub-part a, except replacing 2-methoxybenzoyl chloride with 4-methoxybenzoyl chloride (10 g) the amide was prepared (7.22 g) as a solid: mp 111-113 C.; MS: m/z=166; NMR(CDCl3): 3.0 (d, J=4.9, 3), 3.84 (s,3), 6.90 (m,2), 7.74 (m,2).
With dimethyl amine; In dichloromethane; EXAMPLE 1 4-Methoxy-N-methyl-benzamide (8) An addition funnel containing p-anisoyl chloride (47.6 g, 279 mmol) and methylene chloride (125 mL) was attached to a 2L 3-neck round bottom flask containing 375 mL methylene chloride. The reaction flask was cooled in an ice bath and methylamine (g) was bubbled through the solvent. The contents of the addition funnel were added dropwise. A white precipitate appeared. Warmed to room temperature and stirred for 24 h. Washed with water; separated layers and dried the organic portion with sodium sulfate (anh.). Removal of the solvent in vacuo followed by trituration with hexane/ether gave 8 as a white solid (33.7 g, 204 mmol, 73.2%) 1H-NMR (CHCl3, 300 MHz) δ 7.80 (d, 2H); 6.95 (d, 2H); 6.10 (s, br, 1H); 3.85 (s, 3H), 3.00 (d, 3H).
  • 15
  • [ 3400-22-4 ]
  • [ 92753-20-3 ]
YieldReaction ConditionsOperation in experiment
With sec.-butyllithium; benzaldehyde; In tetrahydrofuran; toluene; EXAMPLE 3 5-Methoxy-3-phenyl-3H-isobenzofuran-1-one (9) A solution of 8 (15 g, 91 mmol) in THF was cooled to -70 C. under Argon. To this was added sec-butyllithium (147 mL, 1.3M). After stirring 0.5 h a tan suspension resulted. Added benzaldehyde (9.2 mL, 91 mmol.) and stirred 1 h. Quenched with ice then removed TiF in vacuo. Added sat. sodium bicarbonate and extracted with ethyl acetate (4*). Dried the combined organic portions with sodium sulfate (anh.) and removed the solvent in vacuo. Added toluene and heated to reflux for 1 h. Removal of the solvent in vacuo followed by trituration with hexane/ether gave unreacted starting material 8 (4.63 g). Concentration of the filtrate in vacuo followed by flash column chromatography (hexane:ethyl acetate 80:20) gave 9 as a yellow solid (12.0 g, 50.1 mmol, 55.1%) 1H-NMR(CHCl3, 300MHz) δ 7.90 (d, 1H); 7.40-7.20 (m, 4H); 7.05 (d, 1H); 6.75 (s, 1H), 6.30 (s, 1H); 3.82 (s, 3H).
  • 16
  • [ 52898-49-4 ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
96% With sodium metal trapped in the nanoscale pores of silica gel; In tetrahydrofuran; at 20℃; for 2h;Glovebox; Sealed tube; Inert atmosphere; General procedure: In a helium-filled glove box, the desired number ofequivalents of Na-AG or Na-SG were added to a round bottom flask, along with aglass-coated stir bar, and the flask sealed with a septum. This closed systemwas then taken out of the glove box, continuously purged with nitrogen, followedby injection of the pure synthesized Weinreb amide dissolved in THF. The resulting mixture was stirred for thetime specified. After completion of the reaction, the mixture was then partitioned using ethyl acetate and brine. The organic layer was concentrated under reducedpressure using a rotary evaporator. 1H NMR of the crude product wastaken to check for reaction extent/completion and to identify the productsobtained. Crude product was fractionated and purified by columnchromatography on silica gel to afford the desired product and byproducts.
  • 17
  • [ 372-48-5 ]
  • [ 52898-49-4 ]
  • [ 79574-74-6 ]
  • [ 3400-22-4 ]
  • 18
  • [ 123-39-7 ]
  • [ 104-92-7 ]
  • [ 3400-22-4 ]
  • 20
  • [ 501-65-5 ]
  • [ 3400-22-4 ]
  • [ 1235478-87-1 ]
YieldReaction ConditionsOperation in experiment
42% With sodium iodide dihydrate; palladium 10% on activated carbon; potassium acetate; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 36h;Schlenk technique; General procedure: A mixture of a substituted benzamide (1) (0.3 mmol, 1.0 equiv),an alkyne (2) (0.6 mmol or 0.9 mmol, 2.0 equiv or 3.0 equiv),10% Pd/C (0.03 mmol, 10 mol%, Alfa Aesar, No. 044696, eggshell,reduced), NaI·2H2O (0.6 mmol, 2.0 equiv), Cs2CO3 (0.3 mmol, 1.0equiv), and KOAc (0.6 mmol, 2.0 equiv) was weighted in a Schlenktube equipped with a stir bar. DMF (1.0 mL) was added and themixture was stirred at 120 C for 36 h under air. Afterwards, themixture was filtered and washed with H2O (30 mL) and extractedwith CH2Cl2 (3×30 mL). The combined organic phase was driedwith anhydrous Na2SO4. After removal of solvents under reducedpressure, the residue was absorbed to small amounts of silica. Thepurification was performed by flash column chromatography onsilica gel with EA:PE (Petroleum ether) = 1:5 or 1:10 as eluent.
  • 21
  • [ 104-92-7 ]
  • [ 14040-11-0 ]
  • [ 6638-79-5 ]
  • [ 52898-49-4 ]
  • [ 3400-22-4 ]
  • 22
  • [ 111-66-0 ]
  • [ 3400-22-4 ]
  • [ 1281888-64-9 ]
  • 23
  • [ 2386-64-3 ]
  • [ 3400-22-4 ]
  • [ 1379242-86-0 ]
  • [ 1309375-45-8 ]
  • 24
  • [ 701-49-5 ]
  • [ 501-65-5 ]
  • [ 3400-22-4 ]
  • [ 1235478-87-1 ]
  • [ 1315257-13-6 ]
YieldReaction ConditionsOperation in experiment
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper(II) acetate monohydrate In tert-Amyl alcohol at 100℃; for 22h; Inert atmosphere;
  • 25
  • [ 201230-82-2 ]
  • [ 3400-22-4 ]
  • [ 63196-45-2 ]
  • 27
  • [ 140-88-5 ]
  • [ 3400-22-4 ]
  • [ 1355020-64-2 ]
  • [ 1355020-74-4 ]
  • 28
  • [ 3400-22-4 ]
  • [ 98-80-6 ]
  • [ 1402849-66-4 ]
  • 29
  • [ 5467-74-3 ]
  • [ 3400-22-4 ]
  • [ 1402849-77-7 ]
  • 30
  • [ 1765-93-1 ]
  • [ 3400-22-4 ]
  • [ 1402849-78-8 ]
  • 31
  • [ 13922-41-3 ]
  • [ 3400-22-4 ]
  • [ 1402849-81-3 ]
  • 32
  • [ 6165-69-1 ]
  • [ 3400-22-4 ]
  • [ 1402849-82-4 ]
  • 33
  • [ 154230-29-2 ]
  • [ 3400-22-4 ]
  • [ 1402849-83-5 ]
  • 34
  • [ 14900-39-1 ]
  • [ 3400-22-4 ]
  • [ 1402849-85-7 ]
  • 35
  • [ 501-65-5 ]
  • [ 6873-44-5 ]
  • [ 3400-22-4 ]
  • [ 1235478-87-1 ]
  • [ 1315257-11-4 ]
  • 36
  • [ 21777-85-5 ]
  • [ 3400-22-4 ]
  • [ 1416562-27-0 ]
  • [ 1416562-28-1 ]
  • 37
  • [ 1315257-09-0 ]
  • [ 501-65-5 ]
  • [ 3400-22-4 ]
  • C22H18(2)HNO [ No CAS ]
  • C23H19(2)H2NO2 [ No CAS ]
  • 38
  • [ 501-65-5 ]
  • [ 3400-22-4 ]
  • 6-methoxy-2-methyl-cis-3,4-diphenyl-3,4-dihydroisoquinolinone [ No CAS ]
  • 6-methoxy-2-methyl-trans-3,4-diphenyl-3,4-dihydroisoquinolinone [ No CAS ]
  • 39
  • [ 3424-93-9 ]
  • [ 80-43-3 ]
  • [ 3400-22-4 ]
  • 40
  • [ 920-46-7 ]
  • [ 3400-22-4 ]
  • 4-methoxy-N-methyl-N-(2-methylacryloyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; triethylamine; In dichloromethane; at 35℃; General procedure: Methacryloyl chloride (2 equiv.) was added to a mixture of amide (1 equiv.), triethylamine (2 equiv.) and DMAP (0.1 equiv.) in dichloromethane (20 mL). The resulted mixture was stirred at 35 oC for 10-12 h. The reaction was quenched with saturated aqueous Na2CO3 (5 mL), and then the mixture was extracted with dichloromethane (3 x 5 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate as the eluent) affording the corresponding N-alkyl-N-methacryloyl benzamides 1.
  • 41
  • [ 61117-58-6 ]
  • [ 74-89-5 ]
  • 4-methoxyphenyl halide (halide-Br/I) [ No CAS ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 0.333333h;Sealed tube; Microwave irradiation; General procedure: To a dry microwave vial, aryl halide (Br, I) (1 eqv.) and amine (2eqv.) were taken in dry 1,4-dioxane. 5 mol% of Pd(OAc)2, 5 mol% ofXantphos and DMAP (2 eqv.) were added followed by (0.25 or 0.3) equivalents ofCo2(CO)8 and the vial was sealed immediately andmicrowave irradiated for 20 min. The reactionmixture was concentrated under reduced pressure, diluted with ethyl acetate andwater, the ethyl acetate layer separated, dried over sodium sulphate, andconcentrated. Thecrude products obtained were subjected to purification by flash chromatographyon silica gel coloumn eluting with petroleum ether and ethyl acetate.
  • 42
  • [ 3400-22-4 ]
  • [ 325685-48-1 ]
  • 43
  • [ 33513-42-7 ]
  • [ 3400-22-4 ]
  • [ 150717-64-9 ]
YieldReaction ConditionsOperation in experiment
80% General procedure: Compounds 2were prepared according to modified known procedure.3 To theappropriate amide (12.5 mmol) stirred in THF (75 mL) at -78 C under argon was added BuLi (27.5 mmol). The solution was held at -78 C for 0.5 h, then allowed to warm to 0 C and kept at 0 C for 6 min. The mixture was cooled to -78 C and DMF (1.280 g, 17.5 mmol) was added. The reaction mixture after 0.5 h at -78 C was warmed to room temperature and kept for 1 h. Then water (15 mL) was added. The mixture was adjusted to pH 2 with hydrochloric acid (2.0 M solution in water) and the organic layer was separated. The water layer was extracted with CHCl3/THF mixture 1:1 (3x15 mL). The combined organic solutions were dried with magnesium sulfate(VI) and evaporated to give the crude products 2. The compounds 2 were purified by crystallization.
  • 44
  • [ 74-11-3 ]
  • [ 3400-22-4 ]
  • [ 1613319-90-6 ]
  • 45
  • [ 65-85-0 ]
  • [ 3400-22-4 ]
  • [ 1613319-91-7 ]
  • 46
  • [ 3400-22-4 ]
  • [ 62-23-7 ]
  • [ 1613319-92-8 ]
  • 48
  • [ 104-93-8 ]
  • [ 33513-42-7 ]
  • [ 7291-00-1 ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
12%; 66% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; zinc dibromide; In acetonitrile; at 80℃; for 16h; General procedure: Under air, in a 50 mL tube, ZnBr2 (20 mol %), TBAI(10 mol%), and a stirring bar was added. Then toluene (10 mmol), DMF (1 mmol), MeCN(2 mL) and TBHP (6 mmol) were injected by syringe. Then close the tube and keepthe final solution at 80 oC for 16 h. When the reaction wasfinished, the solvent was removed in vacuo, and the residue was purified byflash column (petroleum ether/ethyl acetate). All the products are commerciallyavailable.
  • 49
  • [ 61117-58-6 ]
  • [ 74-89-5 ]
  • 4-methoxyhalobenzene [ No CAS ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 90℃; for 0.333333h;Microwave irradiation; General procedure: To a dry microwave vial, aryl halide (Br, I) (1 eqv.) and amine (2 eqv.)were taken in dry 1,4-dioxane. 5 mol% of Pd(OAc)2, 5 mol% ofXantphos and DMAP (2 eqv.) were added followed by (0.25 or 0.3) equivalents ofCo2(CO)8 and the vial was sealed immediately andmicrowave irradiated for 20 min. The reaction mixture was concentrated under reducedpressure, diluted with ethyl acetate and water, the ethyl acetate layerseparated, dried over sodium sulphate, and concentrated. The crude products obtained were subjected topurification by flash chromatography on silica gel coloumn eluting withpetroleum ether and ethyl acetate
  • 50
  • [ 598-32-3 ]
  • [ 3400-22-4 ]
  • 5-methoxy-2-methyl-3-(2-oxopropyl)isoindolin-1-one [ No CAS ]
  • 51
  • [ 140-88-5 ]
  • [ 3400-22-4 ]
  • [ 1355020-64-2 ]
YieldReaction ConditionsOperation in experiment
82% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver(I) acetate; In 1,2-dichloro-ethane; at 60℃; for 13h;Inert atmosphere; General procedure: To a dried screw-capped vial were added benzamide 2 (0.10mmol), ethyl acrylate 3 (0.15mmol), 1b (4.8mg, 0.01mmol), AgSbF6 (6.8mg, 0.02mmol), AgOAc (41.7mg, 0.25mmol), and 1,2-dichloroethane (1.0mL) under Ar atmosphere. The vial was capped and the mixture was heated at 60C for 13h with stirring. After the mixture was cooled to room temperature, saturated EDTA·2Na aqwas added following dilution with CH2Cl2. Organic layer was separated and aqueous layer was extracted with CH2Cl2 (×2). Combined organic layers were dried over Na2SO4. After filtration and evaporation, obtained crude mixture was purified by silica gel column chromatography (CH2Cl2/EtOAc) to give product3.4.1.1 _4.1.3 (E)-Ethyl 3-(5-methoxy-2-(methylcarbamoyl)phenyl)acrylate (4c) A colorless solid; IR (KBr) ν 2985, 2942, 1715, 16,641, 1625, 1546, 1314, 1293, 1228, 1182, 1034, 974, 862 cm-1; 1H NMR (CDCl3, 400 MHz) δ 1.32 (t, J=7.3 Hz, 3H), 2.98 (d, J=5.0 Hz, 3H), 3.83 (s, 3H), 4.24 (q, J=7.3 Hz, 2H), 5.88 (br s, 1H), 6.33 (d, J=16.7 Hz, 1H), 6.89 (dd, J=2.3, 8.7 Hz, 1H), 7.06 (d, J=2.3 Hz, 1H), 7.43 (d, J=8.7 Hz, 1s), 8.02 (d, J=16.5 Hz, 1H); 13C NMR (CDCl3, 100 MHz) δ 14.4, 27.1, 55.6, 60.8, 112.2, 115.4, 121.1, 129.5, 129.7, 135.0, 142.3, 161.0, 166.6, 169.2; HRMS (ESI): m/z calculated for [M+Na]+: 286.1050, found: 286.1054.
  • 52
  • [ 104-93-8 ]
  • [ 74-89-5 ]
  • [ 3400-22-4 ]
YieldReaction ConditionsOperation in experiment
78% With tert.-butylhydroperoxide; iron(III) chloride; tetra-(n-butyl)ammonium iodide; In water; at 60℃; for 24h;Sealed tube; Molecular sieve; Green chemistry; Add 4-methyl anisole (20 eq) to a clean 10 mL sealed tubeAnd methylamine 40% aqueous solution (0.24mmol),TBHP (70% water) 6 eq as oxidant,30 mol% TBAI and 15 mol% FeCl3 are used as catalysts,100 mg of 4A molecular sieve and 1.5 mL of water.React at 60 oC for 24 hours,TLC dot plate detection, after the reaction, the reaction solution is cooled to room temperature,The reaction solution was extracted with ethyl acetate (3×10 mL),Combine the organic phases and dry with anhydrous Na2SO4,The organic layer is concentrated and column chromatography to obtain pureN-methyl 4-methoxybenzamide, yellow solid, yield 78%.
  • 53
  • [ 106-43-4 ]
  • [ 3400-22-4 ]
  • 5-methoxy-N,4'-dimethyl-[1,1'-biphenyl]-2-carboxamide [ No CAS ]
  • 54
  • [ 30004-67-2 ]
  • [ 794-94-5 ]
  • [ 1377585-48-2 ]
  • [ 3400-22-4 ]
  • 55
  • [ 30004-67-2 ]
  • [ 123-11-5 ]
  • [ 1377585-48-2 ]
  • [ 3400-22-4 ]
  • 56
  • [ 104-92-7 ]
  • [ 6638-79-5 ]
  • [ 13939-06-5 ]
  • [ 52898-49-4 ]
  • [ 3400-22-4 ]
  • 57
  • [ 292638-85-8 ]
  • [ 3400-22-4 ]
  • C13H15NO4 [ No CAS ]
  • 58
  • [ 128-53-0 ]
  • [ 3400-22-4 ]
  • 2-(1-ethyl-2,5-dioxopyrrolidin-3-yl)-4-methoxy-N-methylbenzamide [ No CAS ]
  • 59
  • [ 591-87-7 ]
  • [ 3400-22-4 ]
  • 2-allyl-4-methoxy-N-methylbenzamide [ No CAS ]
  • 60
  • [ 38359-28-3 ]
  • [ 123-11-5 ]
  • [ 3400-22-4 ]
  • 62
  • [ 24424-99-5 ]
  • [ 3400-22-4 ]
  • tert-butyl (4-methoxybenzoyl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dmap; In dichloromethane; at 20℃; General procedure: To an oven-dried 100 mL round-bottomed flask containing a secondary amide substrate (1.0 mmol, 1.0 equiv) and DMAP (0.1 mmol, 0.1 equiv) in CH2Cl2 (20 mL) was added Boc2O (1.3 mmol, 1.3 equiv) in one portion and the reaction mixture was allowed to stir at r.t. After the indicated time, the mixture was quenched with aq NaHCO3 (10 mL), and extracted with EtOAc (3 20 mL). the combined organic layers were washed with H2O (20 mL) and brine (20 mL), dried (anhyd Na2SO4), and concentrated. The crude product was purified by column chromatography (EtOAc/PE) to afford the pure product.
  • 63
  • [ 369-57-3 ]
  • [ 3400-22-4 ]
  • [ 1402849-66-4 ]
  • 64
  • [ 201230-82-2 ]
  • [ 19501-58-7 ]
  • [ 74-89-5 ]
  • [ 3400-22-4 ]
  • 66
  • [ 15206-55-0 ]
  • [ 3400-22-4 ]
  • 4-hydroxy-6-methoxy-2-methyl-4-phenylisoquinoline-1,3(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% General procedure: To a stirred solution of 1a (0.14 g, 1.0 mmol) in THF (5mL) at -78 C was added n-BuLi (1.6 M in hexane; 2.0 mmol) dropwise. The temperature was gradually raised to 0 C and stirring was continued for 15 min at the same temperature. The mixture was cooled again to -78 C and PhCOCO2Me (0.16 g, 1.0 mmol) was added dropwise to it. After 5 min, saturated aqueous NH4Cl (15 mL) was added and the resulting mixture was extracted with AcOEt (3 × 10 mL). The combined extracts were washed with brine (10 mL), dried (Na2SO4), and concentrated by evaporation.
  • 67
  • [ 109-94-4 ]
  • [ 3400-22-4 ]
  • C10H11NO3 [ No CAS ]
  • 68
  • [ 2568-65-2 ]
  • [ 3400-22-4 ]
  • ISQ-1 [ No CAS ]
  • 69
  • 2,2,2-trifluoroethyl(2,4,6-trimethylphenyl)iodonium trifluoromethanesulfonate [ No CAS ]
  • [ 3400-22-4 ]
  • 4-methoxy-N-methyl-2-(2,2,2-trifluoroethyl)benzamide [ No CAS ]
  • 70
  • [ 556-61-6 ]
  • [ 3400-22-4 ]
  • 5-methoxy-2-methyl-3-thioxo-2,3-dihydro-1H-isoindol-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% General procedure: To a stirred solution of 1a (0.20 g, 1.5 mmol) in THF (10mL) at -78 C was added n-BuLi (1.6 M in hexane; 3.0 mmol) dropwise and the temperature wasgradually raised to 0 C. After stirring for 1 h at the same temperature, the mixture was cooled to -78 C and MeNCS (0.11 g, 1.5 mmol) was added dropwise. After 5 min, saturated aqueous NH4Cl (25 mL) was added and the mixture was extracted with AcOEt (3 × 15 mL). The combined extracts were washed withbrine (25 mL), dried (Na2SO4), and stood overnight at rt. Concentration of the solution by evaporationgave a residue, which was purified by column chromatography on SiO2 (AcOEt/hexane 1:5) to give theproduct (3a) (0.14 g, 54%); a red solid; mp 95-96 C (hexane/CH2Cl2) (lit.,11 97-98 C ). Spectral (IR, 1H and 13C NMR) data for this compound were identical to those reported previously.3
  • 72
  • [ 5535-48-8 ]
  • [ 3400-22-4 ]
  • C17H15NO4S [ No CAS ]
  • 74
  • [ 637-44-5 ]
  • [ 3400-22-4 ]
  • (E)-4-methoxy-N-methyl-2-styrylbenzamide [ No CAS ]
  • 75
  • [ 86318-61-8 ]
  • [ 3400-22-4 ]
  • [ 153967-91-0 ]
  • 76
  • [ 2170-06-1 ]
  • [ 3400-22-4 ]
  • (E)-4-methoxy-N-methyl-2-styrylbenzamide [ No CAS ]
  • 77
  • [ 110-82-7 ]
  • [ 3400-22-4 ]
  • N-(cyclohexylmethyl)-4-methoxybenzamide [ No CAS ]
  • 78
  • [ 3400-22-4 ]
  • [ 98-80-6 ]
  • [ 92955-84-5 ]
  • 79
  • [ 1679-18-1 ]
  • [ 3400-22-4 ]
  • C15H12ClNO2 [ No CAS ]
  • 80
  • [ 1765-93-1 ]
  • [ 3400-22-4 ]
  • C15H12FNO2 [ No CAS ]
  • 81
  • [ 5720-07-0 ]
  • [ 3400-22-4 ]
  • C16H15NO3 [ No CAS ]
  • 82
  • [ 223463-14-7 ]
  • [ 3400-22-4 ]
  • C14H11BrN2O2 [ No CAS ]
  • 83
  • [ 40339-20-6 ]
  • [ 3400-22-4 ]
  • (E)-5-methoxy-2,3-dimethyl-3-styrylisoindolin-1-one [ No CAS ]
  • 84
  • [ 886-38-4 ]
  • [ 3400-22-4 ]
  • 6'-methoxy-2'-methyl-2-phenylspiro[indene-1,1'-isoindolin]-3'-one [ No CAS ]
  • 85
  • [ 67-56-1 ]
  • [ 3424-93-9 ]
  • [ 3400-22-4 ]
  • 86
  • [ 73183-34-3 ]
  • [ 3400-22-4 ]
  • 4-methoxy-N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
  • 4-methoxy-N-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
  • 87
  • [ 932-31-0 ]
  • [ 3400-22-4 ]
  • 5-methoxy-N, 2'-dimethyl-[1,1'-biphenyl]-2-carboxamide [ No CAS ]
  • 88
  • [ 34589-46-3 ]
  • [ 3400-22-4 ]
  • 5-methoxy-N,2',4'-trimethyl-[1,1'-biphenyl]-2-carboxamide [ No CAS ]
  • 89
  • [ 395-47-1 ]
  • [ 3400-22-4 ]
  • 5-methoxy-N-methyl-2'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide [ No CAS ]
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