3424-93-9

Basic information

• Product Name: 4-Methoxybenzamide
• Synonyms: 4-methoxy-benzamid;Benzamide, 4-methoxy-;4-Methoxybenzamide p-Methoxybenzamide;4-Methoxyphenylformamide;4-Methoxybenzamide,97%;4-ANISAMIDE;4-METHOXYBENZAMIDE;P-ANISAMIDE
• CAS NO: 3424-93-9
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 222-319-6
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Amides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 3424-93-9.mol
• Article Data: 372

Chemical Properties

• Melting Point: 164-167 °C(lit.)
• Boiling Point: 295°C
• Flash Point: 295°C
• Appearance: White/Crystalline Powder
• Density: 1.2023 (rough estimate)
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.5810 (rough estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.34±0.50(Predicted)
• BRN: 1862847
• CAS DataBase Reference: 4-Methoxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxybenzamide(3424-93-9)
• EPA Substance Registry System: 4-Methoxybenzamide(3424-93-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: CV5466666
• Hazardous Substances Data: 3424-93-9(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Synthesis Reference(s)

Journal of the American Chemical Society, 103, p. 6514, 1981 DOI: 10.1021/ja00411a050Synthesis, p. 395, 1975 DOI: 10.1055/s-1975-23770Tetrahedron Letters, 36, p. 7427, 1995 DOI: 10.1016/0040-4039(95)80003-4

InChI:InChI=1/C8H9NO2/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H2,9,10)

Synthetic route

4-methoxybenzonitrile (874-90-8) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With C18H57O3P6Ru2(1+)*C6H5O(1-)*C6H6O; water In 1,4-dioxane for 6h; Time; Sealed tube; Inert atmosphere; Schlenk technique;	100%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); water; 2-(diphenylphosphino)-N,N-dimethylpyridine-4-amine In 1,2-dimethoxyethane at 80℃; for 5h;	99%
With C12H24O16Ru3*2H2O In water at 110℃; for 13h; Catalytic behavior; Schlenk technique; Inert atmosphere;	99%

4-methoxy-benzaldehyde (123-11-5) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With hydroxylamine; C33H28F3N5O3Ru(1+)*Cl(1-) In water at 60℃; for 0.5h; Catalytic behavior; Sonication;	99%
Stage #1: 4-methoxy-benzaldehyde With hydroxylamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 100℃; Stage #2: With palladium diacetate In water; dimethyl sulfoxide at 125℃; chemoselective reaction;	97%
With copper(ll) sulfate pentahydrate; hydroxylamine hydrochloride; sodium acetate at 110℃; for 2h; Neat (no solvent);	97%

4-methoxybenzoic acid (100-09-4) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
Stage #1: 4-methoxybenzoic acid With 1,3,5-trichloro-2,4,6-triazine; potassium carbonate In tetrahydrofuran for 0.0166667h; Milling; Stage #2: With ammonium thiocyanate In tetrahydrofuran for 0.0833333h; Milling;	99%
With pyridine; urea for 0.00833333h; microwave irradiation;	90%
Stage #1: 4-methoxybenzoic acid With thionyl chloride In tetrahydrofuran at 50℃; for 1h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.0833333h;	84%

N-tert-butyl-4-methoxybenzamide (19486-73-8) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
scandium tris(trifluoromethanesulfonate) In nitromethane at 170℃; for 1h; Irradiation;	99%
With t-butyldimethylsiyl triflate In toluene at 100℃; for 8h;	74%

p-hydroxybenzamide (619-57-8) + carbonic acid dimethyl ester (616-38-6) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With dmap at 135℃; under 3000.3 Torr; for 7h; Pressure; Temperature; Reagent/catalyst;	99%

4-methoxy-benzoyl chloride (100-07-2) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With ammonia Inert atmosphere;	98%
With ammonia at -10 - 20℃; for 1h; Temperature;	96.3%
With ammonia In water at 20℃; for 1h;	79%

4-Methoxybenzyl alcohol (105-13-5) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With tert.-butylhydroperoxide; ammonia; oxygen In water; N,N-dimethyl-formamide at 80℃; under 1520.1 Torr; for 5h; Green chemistry;	98%
Stage #1: 4-Methoxybenzyl alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; oxygen; copper(II) nitrate In water; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 5h; Stage #2: With Acetaldehyde oxime In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere;	97%
With ammonia; oxygen In water at 150℃; under 22502.3 Torr; for 3h;	96.5%

4-methoxy-benzylamine (2393-23-9) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With manganese(IV) oxide at 130℃; under 4560.31 Torr; for 3h;	98%
With dihydrogen peroxide at 80℃; for 10h; Inert atmosphere;	96%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium tert-butylate In tert-butyl alcohol at 70℃; for 12h;	95%

4-methoxybenzoyl azide (3532-17-0) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 48h; Ambient temperature;	97%
With 1,3-diadamantane-4,5-dihydroimidazole chloride; potassium tert-butylate; bis(pinacol)diborane; copper(l) chloride In toluene at 25℃; for 4h; Schlenk technique; Inert atmosphere;	94%
With sodium tetrahydroborate; copper(II) sulfate In methanol at 0 - 5℃; for 1h;	92%

4-methoxybenzonitrile (874-90-8) → 4-methoxyphenylacetamide (3424-93-9) + 4-methoxybenzamidoxime (5373-87-5)

Conditions	Yield
With hydroxylamine In ethanol for 3h; Reagent/catalyst; Reflux;	A 97% B n/a
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water Reflux;

1-bromo-4-methoxy-benzene (104-92-7) + carbon monoxide (201230-82-2) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With 2-(2'-pyridyl)(di(1-adamantyl)phosphino)benzene; ammonia; palladium diacetate In 1,4-dioxane at 120℃; under 1500.15 Torr; for 16h; Autoclave;	96%
With tris-(dibenzylideneacetone)dipalladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; ammonium carbamate; sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	93%
With dmap; bis-triphenylphosphine-palladium(II) chloride; formamide In 1,4-dioxane at 120℃; under 3750.38 Torr; for 18h;	69%

1-(4-methoxybenzoyl)piperidine-2,6-dione → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With lithium hydroxide monohydrate In water at 20℃; for 2h;	96%

tert-butyl (4-methoxybenzoyl)carbamate (120158-06-7) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 1h; Ambient temperature;	95%
With trifluoroacetic acid In dichloromethane at 20℃; for 1h; Reagent/catalyst;

carbon monoxide (201230-82-2) + para-iodoanisole (696-62-8) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With ammonium hydroxide; 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane; palladium diacetate In toluene at 130℃; under 5171.62 Torr; Temperature; Autoclave;	95%
With 1,4-diaza-bicyclo[2.2.2]octane; N-methoxylamine hydrochloride; sodium iodide; palladium dichloride In acetonitrile at 90℃; under 3800.26 Torr; for 8h; Autoclave; Inert atmosphere;	93%
With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon; ammonium carbamate; potassium iodide In acetonitrile at 90℃; for 8h; Autoclave; Green chemistry;	90%

p-methoxyl benzaldoxime (3717-21-3, 3717-22-4, 140461-28-5, 140461-29-6, 3235-04-9) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With silver tetrafluoroborate; chloro(1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene)gold(I) at 100℃; for 20h; Beckmann rearrangement; Sealed tube; Neat (no solvent);	95%
With C55H45ClN5P2Ru(1+)*Cl(1-) In water at 110℃; for 12h; Sealed tube;	94%
With C82H80N4O6; mercury dichloride In tetrahydrofuran; water; toluene at 20℃; for 5h; Beckmann Rearrangement;	93%

(Z)-para-methoxybenzaldehyde oxime (3717-22-4) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With toluene-4-sulfonic acid; 1,2-bis-(diphenylphosphino)ethane; carbonyl(dihydro)tris(triphenylphosphine)ruthenium(II) In toluene Heating;	93%
With cerium(III) chloride; silica gel; sodium iodide for 0.0666667h; Beckmann rearrangement; microwave irradiation;	80%

1-bromo-4-methoxy-benzene (104-92-7) + dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
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; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Sealed tube;	93%

2-(4-methoxybenzoylamino)-2-methylpropionic acid (38388-44-2) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With copper dichloride In dimethyl sulfoxide at 120℃; for 11h;	93%
With copper dichloride In dimethyl sulfoxide at 120℃; for 11h;	93%

(E)-4-methoxybenzaldoxime (3717-21-3, 3717-22-4, 3235-04-9, 140461-28-5, 140461-29-6) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 111℃; for 6h;	92%
With indium(III) chloride; 4-methoxybenzonitrile In toluene for 18h; Reflux;	91%
In ethanol for 20h; Quantum yield; Irradiation;

p-Methoxybenzyl bromide (2746-25-0) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
Stage #1: p-Methoxybenzyl bromide With ammonia; iodine In water at 60℃; for 4h; Stage #2: With ammonia; dihydrogen peroxide In water at 0 - 20℃;	92%

4-Methylanisole (104-93-8) + benzylamine (100-46-9) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
Stage #1: benzylamine With N-chloro-succinimide In acetonitrile at 20℃; for 3h; Green chemistry; Stage #2: p-methylanizole With tert.-butylhydroperoxide; iron(II) acetate In decane; acetonitrile at 82℃; for 22h; Green chemistry; Stage #3: With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 12h; Green chemistry;	92%

4-Methylanisole (104-93-8) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With tert.-butylhydroperoxide; iron(III) chloride hexahydrate; tetrabutylammonium iodide; ammonium hydroxide In water at 80℃; for 18h; Sealed tube;	91%
With tert.-butylhydroperoxide; ammonium chloride; calcium carbonate In dihydrogen peroxide; acetonitrile at 80℃; for 10h; Catalytic behavior; Inert atmosphere;	60%

(Z)-para-methoxybenzaldehyde oxime (3717-22-4) + 2 → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 111℃; for 6h;	90%

4-methoxy-benzaldehyde (123-11-5) → 4-methoxyphenylacetamide (3424-93-9) + 4-methoxybenzonitrile (874-90-8) + 4-methoxybenzoic acid (100-09-4)

Conditions	Yield
With H2SO4*2NH2OH; Rh(OH)x/Al2O3 In water for 7h; Heating;	A 90% B 5 % Chromat. C 9 % Chromat.
Stage #1: 4-methoxy-benzaldehyde With pyridine; sodium persulfate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 0.2℃; for 24h; Molecular sieve; Sealed tube; Irradiation; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile for 1h; Molecular sieve;

1-(4-methoxyphenyl)ethanone (100-06-1) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With sodium azide; iodine; sodium hydrogencarbonate In water at 100℃; for 2h; Reagent/catalyst; Temperature; Solvent;	90%
With ammonia; iodine In water at 60℃; for 1h; Lieben-Haller-Bauer reaction;	83%
With ammonia; water; iodine In tetrahydrofuran at 20℃; for 24h; Haller-Bauer reaction;	83%
With sodium azide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper dichloride In water; N,N-dimethyl-formamide at 120℃; under 760.051 Torr; for 15h; Schlenk technique; chemoselective reaction;	67%
With tert.-butylhydroperoxide; ammonia; tetra-(n-butyl)ammonium iodide In water at 100℃; for 16h; Green chemistry;	53%

water (7732-18-5) + 4-methoxybenzonitrile (874-90-8) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With [{Au(SIPr)}2(μ-OH)][BF4] In tetrahydrofuran at 140℃; for 2h; Reagent/catalyst; Concentration; Microwave irradiation;	90%

para-iodoanisole (696-62-8) + potassium ferrocyanide → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With water; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h;	90%

4-methoxyphenylacetylen (768-60-5) → 4-methoxyphenylacetamide (3424-93-9)

Conditions	Yield
With ammonia; dihydrogen peroxide; iodine In water; dimethyl sulfoxide at 20℃; for 3h; Irradiation;	90%

4-methoxy-benzylamine (2393-23-9) → 4-methoxyphenylacetamide (3424-93-9) + 4-methoxybenzonitrile (874-90-8)

Conditions	Yield
With water; oxygen at 140℃; under 3800.26 Torr; for 10h;	A 89% B n/a
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; for 16h;	A 13.6% B 79.3%

4-methoxyphenylacetamide (3424-93-9) → p-methoxythiobenzamide (2362-64-3)

Conditions	Yield
With tetraphosphorus decasulfide In 1,4-dioxane at 50 - 68℃; for 3h; Temperature;	100%
With pyridin-1-ium-1-yl[pyridin-1-ium-1-yl(sulfido)phosphinothioyl]sulfanyl-sulfido-thioxo-phosphane In acetonitrile for 0.5h; Reflux;	88%
With Lawessons reagent In tetrahydrofuran at 20℃; Reflux;	80%

4-methoxyphenylacetamide (3424-93-9) + benzyl alcohol (100-51-6) → N-benzyl-4-methoxybenzamide (7465-87-4)

Conditions	Yield
With barium trifluoromethanesulfonate In toluene for 18h; Reflux; Inert atmosphere;	100%
With C23H24ClIrN3OS(1+)*F6P(1-); caesium carbonate In toluene at 120℃;	96%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 140℃; for 12h;	84%

4-methoxyphenylacetamide (3424-93-9) → 4-methoxybenzonitrile (874-90-8)

Conditions	Yield
With thionyl chloride; carbonic acid dimethyl ester at 80℃; for 7h; Temperature;	99.2%
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;	97%
With ((1,3,5-triazine-2,4,6-triyl)tris(oxy))tris(triphenylphosphonium) chloride at 140 - 150℃; for 2h;	97%

4-methoxyphenylacetamide (3424-93-9) + benzaldehyde (100-52-7) + sodium 4-methylbenzenesulfinate (824-79-3) → 4-methoxy-N-[phenyl-(toluene-4-sulfonyl)-methyl]-benzamide

Conditions	Yield
With chloro-trimethyl-silane In acetonitrile at 10 - 20℃; for 24h; Inert atmosphere;	99%
With chloro-trimethyl-silane In acetonitrile at 23℃;
With chloro-trimethyl-silane In acetonitrile at 0 - 20℃; Inert atmosphere;

4-methoxyphenylacetamide (3424-93-9) + triethyl((3-ethylpent-3-yl)peroxy)silane → N-ethyl-4-methoxy-benzamide (7403-41-0)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline In benzene at 60℃; for 11h; Inert atmosphere;	99%
With copper(l) iodide; 1,10-Phenanthroline In benzene at 60℃; for 11h; Inert atmosphere;	99%

4-methoxyphenylacetamide (3424-93-9) + 4-methoxy-benzaldehyde (123-11-5) → 4-methoxy-N-(4-methoxybenzyl)benzamide (109163-43-1)

Conditions	Yield
With carbon monoxide In diethyl ether at 150 - 160℃; under 30003 Torr; Sealed tube;	99%
With carbon monoxide; C14H10*Ru(2+)*C11H17O(1-)*F6P(1-) In diethyl ether at 150℃; under 22801.5 Torr; for 22h; Autoclave;	70%

4-methoxyphenylacetamide (3424-93-9) → p-anisidine urea (1566-42-3)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; ammonia In methanol at 0 - 20℃; for 2h; Temperature; Hofmann Rearrangement; Inert atmosphere;	99%

4-methoxyphenylacetamide (3424-93-9) + 4-tolyl iodide (624-31-7) → N-(p-methylphenyl)-p-methoxybenzamide (39192-94-4)

Conditions	Yield
With 2-Phenyl-1,3,2-dioxaborinane In 1,4-dioxane at 115℃; for 30h; Inert atmosphere;	99%

4-methoxyphenylacetamide (3424-93-9) + sodium methylate (124-41-4) → methyl N-(4-methoxyphenyl)carbamate (14803-72-6)

Conditions	Yield
Stage #1: 4-methoxyphenylacetamide; sodium methylate In methanol at 20℃; for 0.25h; Stage #2: With bis(1,3-dimethyl-2-imidazolidinone) hydrotribromide In methanol for 4h; Hofmann Rearrangement; Reflux;	98%
With N-Bromosuccinimide In methanol for 0.166667h; Heating;	87%

3-bromo-1-methylquinolin-2(1H)-one (941-91-3) + 4-methoxyphenylacetamide (3424-93-9) → 4-methoxy-N-(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)benzamide

Conditions	Yield
With copper; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 135℃; for 2h; Ullmann type reaction; Inert atmosphere;	98%
With caesium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 10h;	95%
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃;
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 10h; Inert atmosphere; Sealed tube;

methanol (67-56-1) + 4-methoxyphenylacetamide (3424-93-9) → 4-methoxyacetanilide (51-66-1)

Conditions	Yield
With 3-[4-(diacetoxyiodo)phenoxy]-1-propyl-N,N,N-trimethylammonium 4-methylbenzenesulfonate; potassium hydroxide In chloroform at 0 - 20℃; Hofmann Rearrangement; Inert atmosphere;	98%

4-methoxyphenylacetamide (3424-93-9) → 4-Methoxybenzyl alcohol (105-13-5)

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran at 23℃; for 0.0833333h; Reagent/catalyst; Inert atmosphere; Schlenk technique; chemoselective reaction;	98%
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction;	92%
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;	82%

4-methoxyphenylacetamide (3424-93-9) + 3-bromo-butanone (814-75-5) → 2-(4-methoxy-phenyl)-4,5-dimethyl-oxazole (124811-80-9)

Conditions	Yield
With silver(I) trifluoromethoxide In ethyl acetate at 50℃; for 4h; Darkness;	98%

4-methoxyphenylacetamide (3424-93-9) + 2-(1-cyclohexenyl)ethylamine (3399-73-3) → N-(2-(cyclohex-1-en-1-yl)ethyl)-4-methoxybenzamide

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	98%

4-methoxyphenylacetamide (3424-93-9) + α-bromoacetophenone (70-11-1) → 2-(4-methoxyphenyl)-4-phenyloxazole (25205-87-2)

Conditions	Yield
With silver(I) trifluoromethoxide In ethyl acetate at 50℃; for 4h; Reagent/catalyst; Temperature; Darkness;	97%
at 140℃; for 1h;	80%
With silver trifluoromethanesulfonate In ethyl acetate at 50℃; Inert atmosphere;	64%
Heating;

ethyl Bromopyruvate (70-23-5) + 4-methoxyphenylacetamide (3424-93-9) → ethyl 2-(4-methoxyphenyl)-1,3-oxazole-4-carboxylate (78979-61-0)

Conditions	Yield
With silver hexafluoroantimonate In 1,2-dichloro-ethane at 90℃; for 2h; Inert atmosphere; Microwave irradiation;	97%
With silver hexafluoroantimonate In dichloromethane at 90℃; under 3750.38 Torr; for 1h; Sealed tube; Microwave irradiation;
In ethanol at 70℃; for 5h;
Stage #1: ethyl Bromopyruvate; 4-methoxyphenylacetamide With sodium hydrogencarbonate In tetrahydrofuran at 60℃; for 23h; Stage #2: With trifluoroacetic anhydride In tetrahydrofuran at 20℃; for 12h;

4-methoxyphenylacetamide (3424-93-9) + di-tert-butyl dicarbonate (24424-99-5) → N,N-di-Boc-4-methoxybenzamide

Conditions	Yield
With dmap In neat (no solvent) for 4h; Milling; chemoselective reaction;	97%
With dmap In acetonitrile at 20℃; for 15h; Inert atmosphere; Sealed tube;	90%
With dmap In acetonitrile at 20℃; for 15h;	86%

formaldehyd (50-00-0) + 4-methoxyphenylacetamide (3424-93-9) → 5-(4-methoxy)phenyl-1,3,4-oxadiazol-2(3H)-one (41125-75-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium cerium (IV) nitrate; nickel diethyldithiocarbamate; N-fluorobis(benzenesulfon)imide; 1-butyl-methylpyrrolidinium bis(trifluoromethylsulfonyl)amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 60℃; for 10h;	96.8%

4-methyleneoxetan-2-one (674-82-8) + 4-methoxyphenylacetamide (3424-93-9) → 4-Methoxy-N-(3-oxo-butyryl)-benzamide (77656-07-6)

Conditions	Yield
With Aliquat 336 In toluene for 10h; Heating;	96%
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 2h; Ambient temperature;	90%
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 2h; Ambient temperature;	89.5%

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 420-05-3 cyanic acid 
• 100-66-3 methoxybenzene 
• 463-72-9 carbamic chloride 
• 874-90-8 4-methoxybenzonitrile 
• 100-09-4 4-methoxybenzoic acid 
• 57-13-6 urea 
• 123-11-5 4-methoxy-benzaldehyde 
• 136123-73-4 2-(2,4-difluorophenyl)-4-hydroperoxy-4,5-bis(4-methoxyphenyl)imidazole 
• 201230-82-2 carbon monoxide 
• 696-62-8 para-iodoanisole 
• 3717-22-4 (Z)-para-methoxybenzaldehyde oxime 
• 7664-41-7 ammonia 

Downstream Products

• 838-34-6 2-(p-methoxyphenyl)benzoxazole 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 
• 87693-85-4 methyl 2-cyano-3-methylthio-3-N-p-methoxybenzoylaminoacrylate 
• 118996-51-3 (Z)-2-Cyano-3-(4-methoxy-benzoylamino)-3-methylsulfanyl-acrylic acid methyl ester 
• 111860-91-4 4-Hydroxy-2-(4-methoxy-phenyl)-5-methyl-[1,3]oxazin-6-one 
• 94-30-4 ethyl 4-methoxybenzoate 
• 99883-78-0 2-(p-methoxyphenyl)-4-(pentafluoroethyl)-5-(trifluoromethyl)-6,6-difluorooxazine 
• 132606-56-5 (4-Methoxy-benzoyl)-carbamic acid benzyl ester 
• 27562-82-9 diethyl anisoylphosphoramidate 
• 86245-32-1 1-(4-methoxy-benzamidomethyl)-4-nitrobenzimidazole 
• 2362-64-3 p-methoxythiobenzamide 
• 81592-99-6 5-carbamoyl-2-methoxybenzenesulfonyl chloride 
• 58734-14-8 4-methoxy-N-tosylbenzamide 
• 123-11-5 4-methoxy-benzaldehyde 

Relevant articles and documents

The Acid-Catalyzed and Uncatalyzed Hydrolysis of Nitriles on Unactivated Alumina

Nitriles are selectively converted into amides on unactivated alumina, with the surface hydroxyl groups serving as the source of water.

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride

The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.