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104-04-1 Usage

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 104-04-1 differently. You can refer to the following data:
1. Manufacture of nitraniline.
2. 4-Nitroacetanilide was used as a test substrate and its hydrolysis was determined by UV spectroscopic measurements. It was also used to prepare 4-aminoacetanilide.

Preparation

Preparation of 4'-Nitroacetanilide from acetanilide. Principle: Aromatic compounds can be conveniently nitrated by the use of the nitrating mixture, which is normally a mixture of concentrated nitric acid and concentrated sulphuric acid. The function of sulphuric acid is to convert nitric acid into a highly reactive, electrophilic, nitronium ion, NO2+, which is the effective nitrating agent. Nitration of activated aromatic compounds is carried out under milder condition whereas deactivated rings require drastic conditions. Activating groups are o, p-directing, while deactivating groups are m-directing for electrophilic substitution. Reaction: Procedure: Take 0.5 g acetanilide in 0.6 ml glacial acetic acid and add 1 ml conc. H2SO4 in a beaker. Cool the mixture in ice salt bath (5-10°C). To this add a mixture of 0.2 ml conc. H2SO4 and 0.25 ml conc. HNO3 dropwise. Maintain the temperature below 10°C during addition. After addition is over allow the mixture to attain room temperature and leave it for 30 minutes. Pour the mixture on to crushed ice (20 g) with stirring. Filter the separated product and wash with cold water. Dry the product, record the practical yield and re-crystallize it. Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC (using toluene as solvent).

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 5905, 1953 DOI: 10.1021/ja01119a037Tetrahedron Letters, 28, p. 1669, 1987 DOI: 10.1016/S0040-4039(00)95389-9

Purification Methods

Precipitate the anilide from 80% H2SO4 by adding ice, then wash with water, and crystallise from aqueous EtOH. Dry it in air. [Beilstein 12 IV 1632.]

Check Digit Verification of cas no

The CAS Registry Mumber 104-04-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 104-04:
(5*1)+(4*0)+(3*4)+(2*0)+(1*4)=21
21 % 10 = 1
So 104-04-1 is a valid CAS Registry Number.

104-04-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Alfa Aesar

  • (A13539)  4'-Nitroacetanilide, 98%   

  • 104-04-1

  • 5g

  • 195.0CNY

  • Detail
  • Alfa Aesar

  • (A13539)  4'-Nitroacetanilide, 98%   

  • 104-04-1

  • 25g

  • 615.0CNY

  • Detail
  • Aldrich

  • (130648)  4-Nitroacetanilide  98%

  • 104-04-1

  • 130648-5G

  • 279.63CNY

  • Detail

104-04-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4'-NITROACETANILIDE

1.2 Other means of identification

Product number -
Other names 4‘-Nitroacetanilide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-04-1 SDS

104-04-1Synthetic route

4-nitro-aniline
100-01-6

4-nitro-aniline

acetyl chloride
75-36-5

acetyl chloride

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 16h;99.5%
With pyridine In dichloromethane at 0 - 20℃; for 1h;97%
In water at 80℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;96%
Acetanilid
103-84-4

Acetanilid

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With sodium nitrate; sulfuric acid at 0 - 5℃; for 3h;99%
With ammonium molybdate; water; nitric acid In chloroform for 6h; Nitration; Heating;99%
With nitric acid; cetyltrimethylammonim bromide In acetonitrile at 24.84℃; for 2h; Micellar solution; regioselective reaction;85%
p-nitroacetophenone oxime
10342-64-0

p-nitroacetophenone oxime

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With chlorosulfonic acid In toluene at 90℃; for 0.5h; Beckmann rearrangement;99%
With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 2h; Beckmann Rearrangement; Inert atmosphere;94%
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In acetonitrile at 20℃; Beckmann Rearrangement;93%
acetic anhydride
108-24-7

acetic anhydride

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With aluminum oxide at 25℃; for 0.666667h;98%
With lanthanum(III) nitrate at 20℃; for 0.25h;98%
In ethyl acetate at 20℃; for 20h; Inert atmosphere;98%
N-(4-nitrophenyl)ethanethioamide
10319-77-4

N-(4-nitrophenyl)ethanethioamide

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With bismuth(III) nitrate In acetonitrile for 0.166667h; Heating;98%
With acidified wet silica gel; tetrabutylammonium periodite at 20℃; for 0.0333333h; Neat (no solvent);97%
at 20℃; for 0.0833333h; Neat (no solvent);96%
4-nitro-aniline
100-01-6

4-nitro-aniline

diethyl malonate
105-53-3

diethyl malonate

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
Stage #1: 4-nitro-aniline; diethyl malonate at 100 - 130℃;
Stage #2: With caesium carbonate In 1,4-dioxane at 100℃;
98%
acetic acid
64-19-7

acetic acid

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With manganese(III) acetate; ammonium thiocyanate at 25℃; for 2h;95%
With Starbon-400-SO3H at 130℃; for 0.0333333h; Microwave irradiation; chemoselective reaction;92%
With palladium (II) nanoparticles supported on Schiff-base modified clinoptilolite nanocatalyst In neat (no solvent) at 20℃; for 0.25h; Green chemistry; chemoselective reaction;92%
4-nitroacetophenone oxime
59862-56-5

4-nitroacetophenone oxime

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 70℃; for 3h; Beckmann rearrangement; Inert atmosphere;94%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid In water; acetonitrile at 23℃; for 24h; Inert atmosphere;92%
With sodium azide; sulfuric acid; silica gel at 60℃; for 0.75h; Schmidt reaction;90%
With formic acid; hydroxylamine hydrochloride; silica gel at 80℃; for 4h; Beckmann Rearrangement;90%
N-acetyl-p-phenylenediamine
122-80-5

N-acetyl-p-phenylenediamine

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux;92%
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h;86%
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h;80%
With sodium perborate In acetic acid at 50 - 60℃; for 2h;55%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

thioacetic acid
507-09-5

thioacetic acid

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With 2,6-dimethylpyridine In water; acetonitrile at 80℃; Microwave irradiation;88%
With 2,6-dimethylpyridine In water at 80℃; for 0.166667h; Microwave irradiation;
Acetanilid
103-84-4

Acetanilid

A

o-nitroacetanilide
552-32-9

o-nitroacetanilide

B

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h;A 14%
B 86%
With bismuth (III) nitrate pentahydrate; acetic anhydride In dichloromethane at 23℃; for 3h; Solvent; Temperature; Reagent/catalyst; regioselective reaction;A 81%
B n/a
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 6h; Ionic liquid;A 22%
B 71%
p-nitroacetophenone oxime
10342-64-0

p-nitroacetophenone oxime

A

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

B

N-methyl-4-nitrobenzamide
2585-23-1

N-methyl-4-nitrobenzamide

Conditions
ConditionsYield
With silica gel; caesium carbonate; N-tosylimidazole In N,N-dimethyl-formamide for 2h; Beckmann rearrangement; Reflux;A 86%
B 8%
ethyl acetate
141-78-6

ethyl acetate

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With [Zn(BH4)2(py)] In tetrahydrofuran for 5h; Heating;85%
With aluminum (III) chloride; triethylamine at 25℃; for 0.333333h;74%
copper diacetate
142-71-2

copper diacetate

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
In acetic acid for 4.5h; Reflux; chemoselective reaction;85%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With sulphuric acid immobilized on silica gel In neat (no solvent) at 70℃; for 8h; Green chemistry;85%
With Imidazole hydrochloride at 150℃; for 4h; Sealed tube;63%
With potassium tert-butylate at 20℃; Sealed tube; Inert atmosphere;47%
C22H25N4O4(1+)*F6P(1-)

C22H25N4O4(1+)*F6P(1-)

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With trifluoroacetic acid for 8h;82%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

acetic anhydride
108-24-7

acetic anhydride

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With aluminium(III) iodide In acetonitrile for 0.416667h; Heating;80%
4-nitro-aniline
100-01-6

4-nitro-aniline

thioacetic acid
507-09-5

thioacetic acid

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With copper(II)-grafted guanidine acetic acid-modified magnetite nanoparticles In water at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;80%
With Fe3O4(at)Chit-TCT-Salen-Cu(II) In water at 20℃; for 0.0833333h;80%
With copper(ll) sulfate pentahydrate In methanol at 20℃; for 0.0833333h;57%
2,4,6-triacetyloxy-1,3,5-triazine
13483-16-4

2,4,6-triacetyloxy-1,3,5-triazine

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
at 25℃; for 0.166667h; neat (no solvent);77%
acetamide
60-35-5

acetamide

4-nitro-aniline
100-01-6

4-nitro-aniline

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With [Ru-NHC] In toluene at 110℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;76%
With sulfated tungstate In toluene for 24h; Reflux; Green chemistry;74%
With C28H26ClN3ORuS In 1,4-dioxane at 100℃; for 8h; Sealed tube; Inert atmosphere;74%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 120℃; for 1.33333h; Microwave irradiation;56%
4-nitro-aniline
100-01-6

4-nitro-aniline

acetone
67-64-1

acetone

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With chloroform; dimethyl sulfoxide at 120℃; for 24h; Green chemistry;75%
With chloroform; copper(II) acetate monohydrate In dimethyl sulfoxide at 120℃; for 14h; Green chemistry; chemoselective reaction;73%
N′-(4-nitrophenyl)-N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzimidamide
1459721-91-5

N′-(4-nitrophenyl)-N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzimidamide

acetic acid
64-19-7

acetic acid

A

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

B

N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzamide
1403990-53-3

N-(1,7-dihydro-7-oxo-1,3-diphenylbenzo[e][1,2,4]triazin-6-yl)benzamide

C

8-(4-nitrophenyl)-1,3,7-triphenyl-4,8-dihydro-1H-imidazo[4,5-g][1,2,4]benzotriazin-4-yl
1459722-04-3

8-(4-nitrophenyl)-1,3,7-triphenyl-4,8-dihydro-1H-imidazo[4,5-g][1,2,4]benzotriazin-4-yl

Conditions
ConditionsYield
at 120℃; for 1h;A 33%
B 70%
C 13%
4-nitro-aniline
100-01-6

4-nitro-aniline

acetylacetone
123-54-6

acetylacetone

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With dihydrogen peroxide In water at 70℃; for 8h; Green chemistry;69%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium t-butanolate In toluene at 100℃; for 16h;50%
acetic anhydride
108-24-7

acetic anhydride

1,2-bis(p-nitrophenylazo)cyclohexene
203380-92-1, 114263-18-2

1,2-bis(p-nitrophenylazo)cyclohexene

A

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

B

4-acetoxy-2-(p-nitrophenyl)-4,5,6,7-terahydro-2H-benzo<1,2,3>triazole
74733-96-3

4-acetoxy-2-(p-nitrophenyl)-4,5,6,7-terahydro-2H-benzo<1,2,3>triazole

C

N-(4-Nitro-phenyl)-N-[2-(4-nitro-phenyl)-4,5,6,7-tetrahydro-2H-benzotriazol-4-yl]-acetamide
74733-95-2

N-(4-Nitro-phenyl)-N-[2-(4-nitro-phenyl)-4,5,6,7-tetrahydro-2H-benzotriazol-4-yl]-acetamide

Conditions
ConditionsYield
In acetic acid for 0.25h; Ambient temperature;A 25%
B 25%
C 67%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

dimethylglyoxal
431-03-8

dimethylglyoxal

A

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

B

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With Me4NPF4 In N,N-dimethyl-formamide Product distribution; Mechanism; electrolytic reduction at a Pt gauze electrode at a potential of -0.30 V; other supporting electrolytes;A 37%
B 67%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

A

p-nitroacetophenone oxime
10342-64-0

p-nitroacetophenone oxime

B

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; under 1292.9 Torr; for 0.25h; Microwave irradiation;A 10%
B 67%
(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

A

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

B

N-methyl-4-nitrobenzamide
2585-23-1

N-methyl-4-nitrobenzamide

Conditions
ConditionsYield
With sodium hydrogen sulfate; hydroxylamine hydrochloride; silica gel for 0.0333333h; Heating;A 18%
B 62%
With phosphorus pentaoxide; sodium azide; silica gel for 0.166667h; Schmidt reaction; microwave irradiation;
4-Acetamido-1-iodobenzene
622-50-4

4-Acetamido-1-iodobenzene

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

Conditions
ConditionsYield
With copper bronze; tetrabutylammonium nitrate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide at 100℃;57%
4-tert-butylacetanilide
20330-45-4

4-tert-butylacetanilide

A

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

B

N-(4-(tert-butyl)-2-nitrophenyl)acetamide
40655-37-6

N-(4-(tert-butyl)-2-nitrophenyl)acetamide

Conditions
ConditionsYield
With nitric acid at 0℃;A 10%
B 56%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

N-acetyl-p-phenylenediamine
122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With hydrazine hydrate; nickel In methanol for 6h;100%
With indium; acetic acid In tetrahydrofuran Heating;100%
With trimethylamine-borane; palladium hydroxide - carbon In methanol for 3.5h; Heating;99%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

p-nitrobenzene diazonium nitrate

p-nitrobenzene diazonium nitrate

Conditions
ConditionsYield
With Nitrogen dioxide at 5℃;100%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

4-nitroaniline hydrochloride
15873-51-5

4-nitroaniline hydrochloride

Conditions
ConditionsYield
With thionyl chloride In methanol for 0.1h; Reflux;99.8%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

N-(2-chloro-4-nitrophenyl)acetamide
881-87-8

N-(2-chloro-4-nitrophenyl)acetamide

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.166667h; Green chemistry;99%
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h;73%
With chromium(VI) oxide; hydrogenchloride; acetic acid Ambient temperature;58%
formaldehyd
50-00-0

formaldehyd

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

N-4-[methyl-1-(4-bromobenzyl)-4-acetamido]aniline

N-4-[methyl-1-(4-bromobenzyl)-4-acetamido]aniline

Conditions
ConditionsYield
Stage #1: N-(4-Nitrophenyl)acetamide With Decaborane; acetic acid; palladium on activated charcoal In methanol for 0.5h; Heating;
Stage #2: 4-bromo-benzaldehyde With Decaborane In methanol at 20℃; for 0.5h;
Stage #3: formaldehyd With Decaborane In methanol; water at 20℃; for 0.5h;
99%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

m-acetamide aniline
102-28-3

m-acetamide aniline

Conditions
ConditionsYield
With iron(III)-acetylacetonate; hydrazine hydrate In methanol at 150℃; Microwave irradiation; Green chemistry;99%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

mesityl(2-(pentafluoro-λ6-sulfaneyl)pyridyl)-6-iodonium trifluoromethanesulfonate

mesityl(2-(pentafluoro-λ6-sulfaneyl)pyridyl)-6-iodonium trifluoromethanesulfonate

N-(4-nitrophenyl)-N-(6-(pentafluoro-λ6-sulfaneyl)pyridin-2-yl)acetamide

N-(4-nitrophenyl)-N-(6-(pentafluoro-λ6-sulfaneyl)pyridin-2-yl)acetamide

Conditions
ConditionsYield
With sodium hydride In toluene at 20℃; for 10h; Schlenk technique; Inert atmosphere;98%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

N-(2,6-dichloro-4-nitrophenyl)acetamide
17742-68-6

N-(2,6-dichloro-4-nitrophenyl)acetamide

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.583333h; Green chemistry;97.5%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With ammonium iodide; hydrazine hydrate In ethanol at 60℃; for 42h; Inert atmosphere; Sealed tube;97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating;96%
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent);94%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

2,4-dinitroacetanilide
610-53-7

2,4-dinitroacetanilide

Conditions
ConditionsYield
With ammonium molybdate; water; nitric acid In chloroform for 6h; Nitration; Heating;97%
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;94%
With sulfuric acid; nitric acid at 0℃; for 1h;
formaldehyd
50-00-0

formaldehyd

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

butanone
78-93-3

butanone

(N-sec-butyl-N-methylamino)-4-acetamidoaniline
100799-95-9

(N-sec-butyl-N-methylamino)-4-acetamidoaniline

Conditions
ConditionsYield
Stage #1: N-(4-Nitrophenyl)acetamide; butanone With Decaborane; palladium on activated charcoal In methanol for 0.5h; Heating;
Stage #2: With Decaborane In methanol at 20℃; for 2h;
Stage #3: formaldehyd With Decaborane In methanol; water at 20℃; for 1.5h;
95%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

5-methyl-1-(4-nitrophenyl)-1H-tetrazole
40746-65-4

5-methyl-1-(4-nitrophenyl)-1H-tetrazole

Conditions
ConditionsYield
With picoline; diphenyl phosphoryl azide for 16h; Reagent/catalyst; Reflux; Inert atmosphere;95%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With [Zn(BH4)2(py)] In tetrahydrofuran for 3.1h; Heating;94%
With mineral acid durch elektrolytische Reduktion;
With hydrogenchloride; tin
Di-tert-butyl acetylenedicarboxylate
66086-33-7

Di-tert-butyl acetylenedicarboxylate

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

triphenylphosphine
603-35-0

triphenylphosphine

di-tert-butyl 2-(4-nitroacetanilide-N1-yl)-3-(triphenylphosphanylidene)butanedioate

di-tert-butyl 2-(4-nitroacetanilide-N1-yl)-3-(triphenylphosphanylidene)butanedioate

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 6h;94%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

acetic anhydride
108-24-7

acetic anhydride

N,N'-diacetyl-1,4-phenylenediamine
140-50-1

N,N'-diacetyl-1,4-phenylenediamine

Conditions
ConditionsYield
Stage #1: N-(4-Nitrophenyl)acetamide With sodium tetrahydroborate; water In neat (no solvent) at 20℃; for 0.0166667h;
Stage #2: acetic anhydride In neat (no solvent) at 40℃; for 0.0666667h; Reagent/catalyst;
94%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

butanone
78-93-3

butanone

N-(4-(sec-butylamino)phenyl)acetamide
317321-35-0

N-(4-(sec-butylamino)phenyl)acetamide

Conditions
ConditionsYield
With Decaborane; 10percent Pd/C In methanol for 2.5h; Reduction; Reductive amination;91%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

triphenylphosphine
603-35-0

triphenylphosphine

dimethyl 2-(4-nitroacetanilide-N1-yl)-3-(triphenylphosphanylidene)butanedioate

dimethyl 2-(4-nitroacetanilide-N1-yl)-3-(triphenylphosphanylidene)butanedioate

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 6h;91%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

triphenylphosphine
603-35-0

triphenylphosphine

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(4-nitroacetanilide-N1-yl)-3-(triphenylphosphanylidene)butanedioate

diethyl 2-(4-nitroacetanilide-N1-yl)-3-(triphenylphosphanylidene)butanedioate

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 6h;91%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

benzene
71-43-2

benzene

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 50℃; for 3h; Friedel Crafts acylation; Inert atmosphere;91%
With trifluorormethanesulfonic acid In dichloromethane at 50℃; for 3h;91%
N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

sodium 4-methylbenzenesulfinate
824-79-3

sodium 4-methylbenzenesulfinate

N-(4-(4-methylphenylsulfonamido)phenyl)acetamide
27022-64-6

N-(4-(4-methylphenylsulfonamido)phenyl)acetamide

Conditions
ConditionsYield
With trans-N,N'-dimethyl-1,2-cyclohexyldiamine; sodium hydrogen sulfite; iron(II) chloride In dimethyl sulfoxide at 60℃; for 12h; Sealed tube; Inert atmosphere;90%

104-04-1Relevant articles and documents

Acidified, wet, silica-supported tetrabutylammonium periodate: A convenient and mild reagent for conversion of thioamides to their corresponding amides under solvent-free conditions

Nasr-Esfahani, Masoud,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Boostanifar, Mohammad Hasan

, p. 2004 - 2009 (2009)

A series of thioamides are transformed to their corresponding oxo analogues in good to excellent yields with acidified, wet, silica-supported tetrabutylammonium periodate under solvent-free conditions.

-

Holleman,Sluiter

, p. 210 (1906)

-

-

Witt,Utermann

, (1908)

-

NOVEL DESULFURIZATION OF THIOCARBONYL COMPOUNDS INTO THEIR CORRESPONDING OXO-DERIVATIVES USING A PEROXY-SULFUR INTERMEDIATE GENERATED FROM 2-NITROBENZENESULFONYL CHLORIDE AND SUPEROXIDE ANION.

Kim, Yong Hae,Chung, Bong Chul,Chang, Hae Sung

, p. 1079 - 1082 (1985)

Thiocarbonyl compounds such as substituted-thioureas, -thioamides, and -thiocarbamates were found to react with a peroxysulfur intermediate (3) which is generated by the treatment of 2-nitrobenzenesulfonyl chloride with potassium superoxide to convert into the corresponding carbonyl compounds in quantitative yield at -30 oC in acetonitrile.

Synthesis of ring-opened derivatives of triazole-containing quinolinones and their antidepressant and anticonvulsant activities

Song, Ming-Xia,Huang, Yu-Shan,Zhou, Qiu-Gui,Deng, Xian-Qing,Yao, Xiao-Dong

, (2021)

Based on the potent antidepressant and anticonvulsant activities of the triazole-containing quinolinones reported in our previous work, a series of ring-opened derivatives of them were designed, synthesized in this work. Their antidepressant and anticonvulsant activities were screened using the forced swimming test (FST) and the maximal electroshock seizure test (MES), respectively. The results showed that compounds 4a, 5a, 6c-6e, 6g-6i, and 7 led to significant reductions in the accumulated immobility time in the FST at a dose of 50 mg/kg. Especially compound 7 exhibited higher levels of efficacy than the reference standard fluoxetine in the FST and the tail suspension test. The results of an open field test excluded the possibility of central nervous stimulation of 7, which further confirmed its antidepressant effect. Meanwhile, compounds 6a-6i and 7 showed different degrees of anticonvulsant activity in mice at the doses range from 300 to 30 mg/kg in the MES. Among them, compounds 6e and 7 displayed the ED50 of 38.5 and 32.7 mg/kg in the MES, and TD50 of 254.6 and 245.5 mg/kg, respectively. No one showed neurotoxicity at the dose of 100 mg/kg. The preliminary investigation forward to their mechanism indicated that regulation of GABAergic system might contribute to their anticonvulsive and anti-depressive action.

Synthesis and conformational analysis of N-aryl-N-(3-thienyl)acetamides

Ito, Ai,Asami, Yuki,Asato, Marino,Fukuda, Kazuo,Yamasaki, Ryu,Okamoto, Iwao

, p. 2454 - 2458 (2018)

The cis-trans conformational equilibrium of amides is of interest because it can be used to control functional activity. Here, we designed and synthesized a series of N-(3-thienyl)amides in order to study the factors affecting their conformational equilibrium. NMR studies showed that the major conformer of N-methyl-N-(3-thienyl)amide in solution is the E-form (cis form), as is the case for N-methylacetamide. For N-aryl-N-(3-thienyl)amides bearing an N-phenyl moiety, the major conformers differ depending on not only the relative π-electron density of the N-aryl moiety, but also its size. X-ray analysis showed that their solid-state conformational preferences were similar to those in solution.

Brown,Reagan

, p. 1032 (1947)

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Amirsoleimani, Mina,Khalilzadeh, Mohammad A.,Zareyee, Daryoush

, (2020/08/22)

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.

Z-Selective Fluoroalkenylation of (Hetero)Aromatic Systems by Iodonium Reagents in Palladium-Catalyzed Directed C?H Activation

Bényei, Attila,Domján, Attila,Egyed, Orsolya,Gonda, Zsombor,Novák, Zoltán,Sályi, Gerg?,Tóth, Balázs L.

supporting information, (2021/11/09)

The direct and catalytic incorporation of fluorine containing molecular motifs into organic compounds resulting high-value added chemicals represents a rapidly evolving part of synthetic methodologies, thus this area is in the focus of pharmaceutical and agrochemical research. Herein we report a stereoselective procedure for direct fluorovinylation of aromatic and heteroaromatic scaffolds. This methodology development has been realized by palladium-catalyzed ortho C?H activation reaction of aniline derivatives featuring the regioselectivity via directing groups such as secondary of tertiary amides, ureas or ketones. The application of non-symmetrical aryl(fluoroalkenyl)-iodonium salts as fluoroalkenylating agents allowed mild reaction conditions in general for this transformation. The scope and limitations have been thoroughly investigated and the feasibility has been demonstrated by more than 50 examples.

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