1-azido-3,5-dimethoxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate; palladium In water for 1.5h; Inert atmosphere; | 99% |
With sodium sulfide; water for 0.5h; Reflux; | 96% |
With ammonium hydroxide at 90℃; for 0.5h; | 90% |
With triethylamine; tris[tert-butyl]phosphonium tetrafluoroborate In tetrahydrofuran; water at 20℃; for 15h; Staudinger Azide Reduction; | 94 %Spectr. |
N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol for 20h; Ambient temperature; | 94% |
2-Trimethylsilanyl-ethanesulfonic acid (3,5-dimethoxy-phenyl)-amide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide at 95℃; for 40h; | 93% |
1-chloro-3,5-dimethoxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation; | 93% |
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; | 88% |
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Schlenk technique; | 88% |
N-(3,5-dimethoxy-phenyl)-acetamide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: N-(3,5-dimethoxy-phenyl)-acetamide With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; Stage #2: With water In tetrahydrofuran Inert atmosphere; chemoselective reaction; | 86% |
With alkaline solution |
3,5-dimethoxyphenylboronic acid
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h; | 82% |
1-bromo-3,5-dimethoxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3,5-dimethoxybenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere; | 78% |
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; Sealed tube; | 68% |
With ammonia; sodium; ferric nitrate |
1-iodo-3,5-dimethoxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube; | 75% |
3,5-dimethoxyphenol
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 3,5-dimethoxyphenol With Nonafluorobutanesulfonyl fluoride; tris(trimethylsilyl)amine; potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 5h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; for 0.0833333h; pH=3 - 4; Reagent/catalyst; Solvent; | 75% |
3,5-dimethoxybenzoic acid
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 3,5-dimethoxybenzoic acid With diphenylphosphoranyl azide; triethylamine In toluene at 80℃; Stage #2: With sodium hydroxide In tetrahydrofuran; toluene at 20℃; for 2h; | 43% |
Stage #1: 3,5-dimethoxybenzoic acid With diphenylphosphoranyl azide; triethylamine In toluene at 80℃; Stage #2: With sodium hydroxide In tetrahydrofuran for 2h; | 43% |
N-hydroxy-3,5-dimethoxybenzamide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: N-hydroxy-3,5-dimethoxybenzamide With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 50℃; for 2h; Lossen Rearrangement; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃; | 3% |
Stage #1: N-hydroxy-3,5-dimethoxybenzamide With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.0833333h; |
1-Bromo-2,4-dimethoxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With ammonia; sodium amide in fluessiges NH3; |
1,3-dimethoxy-5-nitrobenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With hydrogenchloride; tin | |
With hydrogenchloride; tin; tin(ll) chloride at 40℃; Reagens 5: Essigsaeure; | |
With ethanol; nickel Hydrogenation; | |
With hydrogen; palladium on activated charcoal In ethyl acetate |
3,5-dimethoxybenzamide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With sodium hypobromide at -15℃; | |
Yield given; | |
With sodium hypochlorite; sodium hydroxide at 80℃; for 5h; | 4.1 g |
ethyl 3,5-dimethoxybenzoate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 78 percent / hydrazine hydrate / 2 h / Heating 2: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 3: 93 percent / toluene / 2.5 h / Heating 4: 8.7 g / sodium hydroxide (20percent) / 60 °C View Scheme |
3,5-Dihydroxybenzoic acid
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 84 percent / sodium hydroxide / heating View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 55 °C 2.1: triethylamine; diphenylphosphoranyl azide / toluene / 80 °C 2.2: 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 55 °C 2.1: triethylamine; diphenylphosphoranyl azide / toluene / 80 °C 2.2: 2 h View Scheme |
azido(3,5-dimethoxyphenyl)methanone
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 93 percent / toluene / 2.5 h / Heating 2: 8.7 g / sodium hydroxide (20percent) / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: CH2Cl2 / 60 h / Heating 2: 94 percent / H2O, K2CO3 / methanol / 20 h / Ambient temperature View Scheme |
3,5-dimethoxy-benzoic acid hydrazide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C 2: 93 percent / toluene / 2.5 h / Heating 3: 8.7 g / sodium hydroxide (20percent) / 60 °C View Scheme |
3,5-dimethoxybenzoyl chloride
3,5-Dimethoxyaniline
3,5-dimethoxyphenyl isocyanate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 8.7 g / sodium hydroxide (20percent) / 60 °C View Scheme | |
With benzoic acid; sodium hydroxide In tetrahydrofuran at 20℃; for 0.5h; Curtius Rearrangement; |
3,5-dihydroxyphenylamine
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous dioxane 2: aqueous NaOH 3: aq.-ethanolic alkaline solution View Scheme |
N-(3,5-dihydroxyphenyl)acetamide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous NaOH 2: aq.-ethanolic alkaline solution View Scheme |
methyl 3,5-dimethoxybenzoate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: liquid ammonia 2: aqueous sodium hypobromite / -15 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / 1,4-dioxane / 5 h / 20 °C 2: triethylamine; diphenyl phosphoryl azide / 80 °C 3: sodium hydroxide; benzoic acid / tetrahydrofuran / 0.5 h / 20 °C View Scheme |
3,5-dimethoxyphenol
2,3-dimethoxyphenol
diethylazodicarboxylate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With triphenylphosphine In tetrahydrofuran |
1-carbomethoxy-3,5-dihydroxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium carbonate / acetonitrile / 20 °C 2: sodium hydroxide / 1,4-dioxane / 5 h / 20 °C 3: triethylamine; diphenyl phosphoryl azide / 80 °C 4: sodium hydroxide; benzoic acid / tetrahydrofuran / 0.5 h / 20 °C View Scheme |
1-chloro-3,5-dimethoxybenzene
A
bis(3,5-dimethoxyphenyl)amine
B
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Overall yield = 81 %; |
Conditions | Yield |
---|---|
With phosphoric acid; ammonia In ethylene glycol at 145℃; for 5h; | A 95 %Spectr. B 84 %Spectr. |
di-tert-butyl dicarbonate
3,5-Dimethoxyaniline
(3,5-dimethoxyphenyl)-carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Inert atmosphere; | 100% |
Stage #1: 3.5-dimethoxyaniline With triethylamine In dichloromethane at 20℃; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; | 99% |
at 90℃; for 3h; | 98% |
methyl chloroformate
3,5-Dimethoxyaniline
methyl N-(3,5-dimethoxyphenyl)carbamate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 100% |
With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 94% |
In toluene for 2h; Acylation; Heating; | 81% |
4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline
bis(trichloromethyl) carbonate
sodium hydrogencarbonate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With triethylamine In toluene | 100% |
3,5-Dimethoxyaniline
Methacryloyl chloride
N-(3,5-dimethoxyphenyl)-2-methylacrylamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 100% |
In dichloromethane at 0 - 20℃; | |
In dichloromethane at 0 - 20℃; | |
In dichloromethane at 0 - 20℃; | |
With dmap; triethylamine In dichloromethane at 0 - 20℃; |
2-Bromoacetyl bromide
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1.25h; Inert atmosphere; | 100% |
at -77℃; |
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; | 99.9% |
1,1,1-trifluoro-4-phenylbut-3-yn-2-one
3,5-Dimethoxyaniline
(Z)-4-(3,5-Dimethoxy-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one
Conditions | Yield |
---|---|
In methanol Ambient temperature; | 99% |
2-bromo-4'-fluoroacetophenone
3,5-Dimethoxyaniline
2-[(3,5-dimethoxyphenyl)amino]-1-(4-fluorophenyl)ethanone
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In neat (no solvent) at 20℃; for 2h; | 99% |
With sodium hydrogencarbonate In ethanol for 4h; Heating; |
(Z)-ethyl 3-(methylamino)-3-phenylacrylate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 30h; Heating; | 99% |
2-formylphenyl triflate
3,5-Dimethoxyaniline
1,3-dimethoxyacridine
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; XPhos In toluene at 105℃; for 13h; Mechanism; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With acetic acid; zinc at 20 - 60℃; for 2.5h; | 99% |
2-bromo-5-chlorobenzaldehyde
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-5-chlorobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere; | 99% |
2-bromo-5-nitrobenzaldehyde
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-5-nitrobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere; | 99% |
2-bromo-6-fluorobenzaldehyde
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-6-fluorobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: ortho-bromobenzaldehyde In toluene at 80℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere; | 99% |
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: ortho-bromobenzaldehyde In toluene at 80℃; for 12h; Reagent/catalyst; | 99% |
1-bromo-3,5-dimethoxybenzene
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Schlenk technique; | 99% |
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In tetrahydrofuran at 60℃; for 19h; Inert atmosphere; | 81% |
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In tetrahydrofuran at 60℃; Inert atmosphere; | 75% |
3,5-dimethoxyaniline hydrochloride
4,4'-dimethoxybenzoin
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
at 130 - 140℃; for 1h; | 99% |
ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 3.5-dimethoxyaniline With trimethylaluminum In n-heptane; 1,2-dichloro-ethane at 0 - 20℃; for 0.5h; Stage #2: ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate In n-heptane; 1,2-dichloro-ethane for 2h; Reflux; | 99% |
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; toluene for 4h; Reflux; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 16h; Inert atmosphere; | 98.4% |
acetic anhydride
3,5-Dimethoxyaniline
N-(3,5-dimethoxy-phenyl)-acetamide
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; | 98% |
In toluene at 20℃; for 15h; Time; Inert atmosphere; | 98% |
In toluene at 25℃; for 20h; | 97% |
indan-1,2,3-trione hydrate
3,5-Dimethoxyaniline
Conditions | Yield |
---|---|
In acetic acid for 16h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; MS 4 Angstroem; palladium diacetate; triphenylphosphine In benzene at 80℃; for 3h; Alkylation; N-allylation; | 98% |
para-bromotoluene
3,5-Dimethoxyaniline
N-(4-tolyl)-3,5-dimethoxyaniline
Conditions | Yield |
---|---|
With C60H86O4P2Pd2(2+)*2BF4(1-); sodium t-butanolate In 1,4-dioxane at 80℃; for 1h; | 98% |
With sodium t-butanolate; 1,1'-bis(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)palladium In toluene at 90℃; for 5h; |
3,5-Dimethoxyaniline
trifluoroacetic anhydride
N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 1h; | 98% |
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; | 98% |
With triethylamine In toluene at 15 - 20℃; for 1.5h; Temperature; Solvent; | 85.4% |
With triethylamine In toluene at 18 - 25℃; for 2h; | |
With triethylamine In dichloromethane at 20℃; for 2.5h; Cooling with ice; |
ethyl trifluoroacetate,
3,5-Dimethoxyaniline
N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran for 48h; Heating / reflux; | 98% |
With dmap In tetrahydrofuran for 48h; Reflux; | 98% |
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