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Synthetic route

benzofurazan oxide
480-96-6

benzofurazan oxide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With iron(II) sulfate In water; dimethyl sulfoxide Ambient temperature;100%
With HbO2(2+) In phosphate buffer; dimethyl sulfoxide for 1h; pH=7.4;89 % Chromat.
4-methyl-N-(2-nitrophenyl)benzene sulfonamide
6380-13-8

4-methyl-N-(2-nitrophenyl)benzene sulfonamide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 25 - 90℃; for 5.5h; Inert atmosphere;99%
2-Chloronitrobenzene
88-73-3

2-Chloronitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr;98.6%
With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr;98%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h;95%
1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With hydrogen at 20℃; under 760.051 Torr; for 1h;98%
With hydrogen; 1-(2-benzimidazolyl)-C(CH3)=NH-NHCSNH2-Pd(II) In tetrahydrofuran at 20℃; for 2h; atmospheric pressure;95%
With triethylamine In water at 80℃; for 2h; Inert atmosphere; Green chemistry; chemoselective reaction;95%
ortho-nitrobenzoic acid
552-16-9

ortho-nitrobenzoic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1-n-butyl-3-methylimidazolium azide; sulfuric acid; acetic acid at 54℃; for 4h; Schmidt Reaction;97%
With sodium azide; chloroform; sulfuric acid
With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 2h, reflux; Yield given. Multistep reaction;
o-nitroacetanilide
552-32-9

o-nitroacetanilide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating;95%
With sodium hydroxide In ethanol Reflux;80%
With hydrogenchloride; water for 2h; Reflux;77%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 6h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere;95%
Stage #1: 2-nitrophenyl bromide With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h;
Stage #2: With ammonia In water; acetone at 90℃; for 24h;
83%
With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline In dimethyl sulfoxide at 70℃; for 24h;78%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; Reagent/catalyst;95%
With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 20h; pH=11; Green chemistry;86%
With dihydrogen peroxide; potassium carbonate In water; acetonitrile at 20℃;75%
With sodium peroxide
palladium-carbon In triethylene glycol dimethyl ether
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere;
Stage #2: for 4h; Catalytic behavior; Reagent/catalyst; Irradiation; chemoselective reaction;
95%
With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Heating;94%
Stage #1: o-azidonitrobenzene With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; tert-butyl alcohol In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: With sodium t-butanolate In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; chemoselective reaction;
94%
N-(2-nitrophenyl)benzanilide
728-90-5

N-(2-nitrophenyl)benzanilide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating;95%
With lithium aluminium tetrahydride In diethyl ether at 27℃; for 1h;66 % Turnov.
2-(2-nitrophenoxy)propanamide
58562-47-3

2-(2-nitrophenoxy)propanamide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 3h; Green chemistry;95%
2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With potassium carbonate; potassium iodide; Chloroacetamide In N,N-dimethyl-formamide at 90 - 150℃; for 4h; Reagent/catalyst; Smiles Aromatic Rearrangement;92%
With ammonia; water at 160 - 170℃;
With sodium tetrahydroborate In water at 20℃;
2-nitroaniline-4-sulfonic acid
616-84-2

2-nitroaniline-4-sulfonic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With phosphoric acid In sulfolane at 120℃; Reagent/catalyst; Solvent; Temperature;91%
With hydrogenchloride at 170 - 180℃; Erhitzen des Kaliumsalzes;
With sulfuric acid; water
aniline
62-53-3

aniline

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 4h;A 88%
B 12%
With potassium hydrogensulfate; potassium metaperiodate; silica gel; sodium nitrite In neat (no solvent) for 0.0833333h; Reagent/catalyst; Solvent; Microwave irradiation;A 86%
B n/a
With Iron(III) nitrate nonahydrate at 84.84℃; for 0.25h; regioselective reaction;A 77%
B 23%
o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With copper(l) iodide; tetra(n-butyl)ammonium hydroxide; ammonia In water at 25℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;87%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 6h; Sealed tube; Inert atmosphere;84%
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry;82%
2-(trimethylsilanyl)ethanesulfonic acid (2-nitrophenyl)amide
1045771-53-6

2-(trimethylsilanyl)ethanesulfonic acid (2-nitrophenyl)amide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 130℃; for 36h;87%
1-(2-chlorophenyl)-N-(2-nitrophenyl)-1H-tetrazol-5-amine

1-(2-chlorophenyl)-N-(2-nitrophenyl)-1H-tetrazol-5-amine

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 110℃; for 22h;84%
4-tert-butyl-2-(2-nitrophenylazo)phenol
27959-42-8

4-tert-butyl-2-(2-nitrophenylazo)phenol

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

N-formyldiethylamine
617-84-5

N-formyldiethylamine

C

2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole
3147-76-0

2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole

D

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given;A n/a
B n/a
C 63%
D 82%
4-methyl-2-(2-nitrophenylazo)phenol
1435-71-8

4-methyl-2-(2-nitrophenylazo)phenol

A

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

B

5-methylbenzo[d]oxazol-2(3H)-one
22876-15-9

5-methylbenzo[d]oxazol-2(3H)-one

C

2-nitro-aniline
88-74-4

2-nitro-aniline

D

2-(2-Hydroxy-5-methylphenyl)benzotriazole
2440-22-4

2-(2-Hydroxy-5-methylphenyl)benzotriazole

Conditions
ConditionsYield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given;A n/a
B n/a
C 7%
D 82%
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

(3R,4S)-2,3,4,5-Tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole
55520-53-1, 55520-54-2

(3R,4S)-2,3,4,5-Tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole

A

2-nitro-aniline
88-74-4

2-nitro-aniline

2,3,4r,5-tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole 3c-oxide
51849-78-6, 51849-79-7, 64057-39-2, 64057-40-5

2,3,4r,5-tetraphenyl-3,4-dihydro-2H-[1,2,3]diazaphosphole 3c-oxide

C

C32H27N4O3P

C32H27N4O3P

Conditions
ConditionsYield
In benzene for 2h; Ambient temperature;A 20%
B n/a
C 80%
benzofurazan oxide
480-96-6

benzofurazan oxide

thiophenol
108-98-5

thiophenol

A

2-nitro-aniline
88-74-4

2-nitro-aniline

B

N-(2-nitrophenyl)benzensulphenamide

N-(2-nitrophenyl)benzensulphenamide

Conditions
ConditionsYield
With iron(II) sulfate In water; dimethyl sulfoxide for 1.5h; Ambient temperature;A 80%
B 20%
2-[(2-nitrophenyl)amino]ethanol
4926-55-0

2-[(2-nitrophenyl)amino]ethanol

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With ammonium hydroxide; sodium sulfite In methanol at 70℃; for 144h;80%
4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With hydrogen bromide; acetic acid; aniline for 19h; Heating;80%
With sodium acetate In ethanol at 30℃; under 600 Torr; for 0.5h; Reagent/catalyst; Temperature; Inert atmosphere;74.6%
o-azidonitrobenzene
1516-58-1

o-azidonitrobenzene

A

2-nitro-aniline
88-74-4

2-nitro-aniline

B

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere;
Stage #2: for 4h; Irradiation;
A 20%
B 80%
1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

A

2-nitro-aniline
88-74-4

2-nitro-aniline

B

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
Stage #1: 1,2-Dinitrobenzene With sodium tetrahydroborate In water at 20℃; for 0.25h; Inert atmosphere; Green chemistry;
Stage #2: In water at 20℃; for 0.75h; Inert atmosphere; Green chemistry;
A 78%
B 15%
With sodium tetrahydroborate; water at 0 - 20℃; for 24h;A 24%
B 53%
With titanium dioxide In ethanol for 1.5h; Irradiation; Green chemistry;A 55 %Chromat.
B 30 %Chromat.
ammonium hydroxide
1336-21-6

ammonium hydroxide

o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; potassium phosphate tribasic heptahydrate; water; Sucrose In water at 90℃; for 15h; Catalytic behavior; Green chemistry;78%
N-(2-nitrophenyl)-1-phenyl-1H-tetrazol-5-amine

N-(2-nitrophenyl)-1-phenyl-1H-tetrazol-5-amine

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 110℃; for 22h;78%
2-nitrobenzamide
610-15-1

2-nitrobenzamide

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water at 70℃; for 1h;76%
nitrobenzene
98-95-3

nitrobenzene

A

4-nitro-aniline
100-01-6

4-nitro-aniline

B

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h; Product distribution; Mechanism; other sulfenamide reagents, other nitroarenes;A 71%
B 14%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;A 71%
B 14%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide In N,N-dimethyl-formamide at 20℃; for 0.333333h;A 71%
B 14%
phthalic anhydride
85-44-9

phthalic anhydride

2-nitro-aniline
88-74-4

2-nitro-aniline

N-(o-nitrophenyl)phthalimide
34442-94-9

N-(o-nitrophenyl)phthalimide

Conditions
ConditionsYield
In acetic acid at 20℃; for 36h; Heating / reflux;100%
With acetic acid for 24h; Heating;89%
With N,N-dimethyl-formamide for 0.0666667h; microwave irradiation;84%
2-nitro-aniline
88-74-4

2-nitro-aniline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-methyl-N-(2-nitrophenyl)benzene sulfonamide
6380-13-8

4-methyl-N-(2-nitrophenyl)benzene sulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With pyridine In dichloromethane at 20℃; for 48h;90%
With pyridine In dichloromethane at 20℃; for 16h;75%
2-nitro-aniline
88-74-4

2-nitro-aniline

4-iodo-2-nitroaniline
20691-72-9

4-iodo-2-nitroaniline

Conditions
ConditionsYield
With N-iodo-succinimide In acetic acid at 95℃; for 1h;100%
With sodium periodate; potassium iodide; sodium chloride In water; acetic acid at 25℃; for 8h;98%
With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 4h; Reagent/catalyst;98%
2-nitro-aniline
88-74-4

2-nitro-aniline

2-nitrobenzenediazonium tetrafluoroborate
365-33-3

2-nitrobenzenediazonium tetrafluoroborate

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With boron trifluoride diethyl etherate In dichloromethane at -15℃; for 0.25h;
Stage #2: With tert.-butylnitrite In dichloromethane at -15 - 0℃; for 1h;
100%
With tert.-butylnitrite; boron trifluoride diethyl etherate In dichloromethane at 0 - 20℃;95%
With dinitrogen tetraoxide; benzene entsteht das Nitrat;
2-nitro-aniline
88-74-4

2-nitro-aniline

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

Conditions
ConditionsYield
With hydrazine hydrate at 90℃; for 1.16667h; chemoselective reaction;100%
With hydrazine hydrate In ethanol; water at 80℃; for 3h; chemoselective reaction;100%
With sodium tetrahydroborate In water for 0.116667h; Kinetics; Catalytic behavior; Reagent/catalyst;100%
cyanoacetic acid
372-09-8

cyanoacetic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

2-cyano-N-[2-(nitro)phenyl]acetamide
65372-22-7

2-cyano-N-[2-(nitro)phenyl]acetamide

Conditions
ConditionsYield
Stage #1: cyanoacetic acid With phosphorus pentachloride In dichloromethane for 0.5h; Reflux;
Stage #2: 2-nitro-aniline In dichloromethane for 2h; Reflux;
100%
With dicyclohexyldiimide In N,N-dimethyl-formamide for 1h; Ambient temperature;74%
With phosphorus pentachloride In benzene
methyl trans-3-(4-methoxyphenyl)glycidate
96125-49-4

methyl trans-3-(4-methoxyphenyl)glycidate

2-nitro-aniline
88-74-4

2-nitro-aniline

2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylamino)-propionic acid methyl ester
100597-06-6, 100597-07-7

2-Hydroxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylamino)-propionic acid methyl ester

Conditions
ConditionsYield
zinc(II) iodide In toluene at 22℃; for 21h; Product distribution; various solvents, additives, temperatures, times;100%
zinc(II) iodide In toluene at 22℃; for 21h;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-nitro-aniline
88-74-4

2-nitro-aniline

(2-nitro-phenyl)-carbamic acid tert-butyl ester
54614-93-6

(2-nitro-phenyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 1h;
100%
With 12-TPA/SBA 15 at 20℃; for 0.1h; Neat (no solvent);97%
Stage #1: 2-nitro-aniline With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.666667h;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 2h;
96%
2-nitro-aniline
88-74-4

2-nitro-aniline

p-tert-butyl benzoyl chloride
1710-98-1

p-tert-butyl benzoyl chloride

N-(2-nitrophenyl)-4-(1,1-dimethylethyl)-benzamide
219492-27-0

N-(2-nitrophenyl)-4-(1,1-dimethylethyl)-benzamide

Conditions
ConditionsYield
With pyridine Acylation;100%
With pyridine In dichloromethane Acylation;
acetic acid
64-19-7

acetic acid

2-nitro-aniline
88-74-4

2-nitro-aniline

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

Conditions
ConditionsYield
With tin(ll) chloride at 130℃; for 0.0833333h; microwave;100%
With hydrogenchloride; iron In water at 70 - 100℃;
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2-nitro-aniline
88-74-4

2-nitro-aniline

N-(2-chlorophenyl)-N-(2-nitrophenyl)amine
74002-26-9

N-(2-chlorophenyl)-N-(2-nitrophenyl)amine

Conditions
ConditionsYield
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 24h; Buchwald-Hartwig coupling; Inert atmosphere;100%
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Buchwald-Hartwig reaction;99%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; Inert atmosphere;86%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In toluene at 110℃; for 30h;65%
2-nitro-aniline
88-74-4

2-nitro-aniline

trifluoroacetic acid
76-05-1

trifluoroacetic acid

2-Trifluoromethylbenzimidazole
312-73-2

2-Trifluoromethylbenzimidazole

Conditions
ConditionsYield
With tin(ll) chloride at 130℃; for 0.0833333h; microwave;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

2-nitro-aniline
88-74-4

2-nitro-aniline

2-nitrophenyl isocyanate
3320-86-3

2-nitrophenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
In toluene for 3h; Heating;
In dichloromethane at 0℃; for 0.5h;
Cyclopentane
287-92-3

Cyclopentane

carbon monoxide
201230-82-2

carbon monoxide

2-nitro-aniline
88-74-4

2-nitro-aniline

C6H9ONHC6H4NO2

C6H9ONHC6H4NO2

Conditions
ConditionsYield
With aluminum tri-bromide at -20℃;100%
Stage #1: Cyclopentane; carbon monoxide With aluminum tri-bromide; carbon tetrabromide In various solvent(s) at 0℃; under 760.051 Torr; for 4h;
Stage #2: 2-nitro-aniline In various solvent(s) at -20 - 20℃; under 760.051 Torr; Further stages.;
100 % Chromat.
Stage #1: Cyclopentane; carbon monoxide With 2AlBr3*CBr4 In dibromomethane
Stage #2: 2-nitro-aniline In dibromomethane at 0℃; for 2h; chemoselective reaction;
97 %Chromat.
2-thienylacetic acid chloride
39098-97-0

2-thienylacetic acid chloride

2-nitro-aniline
88-74-4

2-nitro-aniline

C12H10N2O3S

C12H10N2O3S

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;100%
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

2-nitro-aniline
88-74-4

2-nitro-aniline

2,2-dimethyl-5-((2-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione
25063-47-2

2,2-dimethyl-5-((2-nitrophenylamino)methylene)-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;100%
2-nitro-aniline
88-74-4

2-nitro-aniline

benzyl alcohol
100-51-6

benzyl alcohol

2-phenyl-1H-benzoimidazole
716-79-0

2-phenyl-1H-benzoimidazole

Conditions
ConditionsYield
With palladium with copper supported on alumina In water at 179.84℃; under 26252.6 Torr; for 12h; Autoclave;100%
With JRC-TIO-7-supported iridium catalyst In 1,3,5-trimethyl-benzene at 80℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 160℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Schlenk technique; Inert atmosphere; Sealed tube;97%
2-nitro-aniline
88-74-4

2-nitro-aniline

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

C12H12N2O6

C12H12N2O6

Conditions
ConditionsYield
at 20℃; for 0.133333h; Milling; Inert atmosphere;100%
2-nitro-aniline
88-74-4

2-nitro-aniline

4-Chloro-2-nitroaniline
89-63-4

4-Chloro-2-nitroaniline

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.0833333h; Green chemistry;99.2%
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 16h; regioselective reaction;85%
With N-chloro-succinimide In acetonitrile for 10h; Heating;57%
Multi-step reaction with 2 steps
1: diethyl ether; hypochlorous acid / 20 °C
2: hydrochloric acid; diethyl ether / -20 °C
View Scheme
benzoyl chloride
98-88-4

benzoyl chloride

2-nitro-aniline
88-74-4

2-nitro-aniline

N-(2-nitrophenyl)benzanilide
728-90-5

N-(2-nitrophenyl)benzanilide

Conditions
ConditionsYield
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 18h;99%
With pyridine at 25℃; for 15h;97%
With pyridine; dmap93%
2-nitro-aniline
88-74-4

2-nitro-aniline

acetyl chloride
75-36-5

acetyl chloride

o-nitroacetanilide
552-32-9

o-nitroacetanilide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃;99%
With montmorillonite K-10 In dichloromethane for 1.5h; Ambient temperature;98%
With carbon-silica composite from starch (7.5 molpercent SO3H) at 60℃; for 0.75h; solvent-free conditions;95%
2-nitro-aniline
88-74-4

2-nitro-aniline

4-Bromo-2-nitroaniline
875-51-4

4-Bromo-2-nitroaniline

Conditions
ConditionsYield
With hydrogen bromide; dihydrogen peroxide In methanol at 0 - 20℃; for 12h;99%
With HMTAB In dichloromethane at 20℃; for 0.5h;98%
With 1-butyl-3-methylpyridinium tribromide at 20℃;98%
2-nitro-aniline
88-74-4

2-nitro-aniline

2,4-dibromo-6-nitroaniline
827-23-6

2,4-dibromo-6-nitroaniline

Conditions
ConditionsYield
With bromine In methanol; dichloromethane at 20℃; for 1h;99%
With bromine; acetic acid at 45℃; for 4h;98%
With bromine; acetic acid at 45℃; for 4h;98%
3-methylbutyric acid trimethylsilyl ester
55557-13-6

3-methylbutyric acid trimethylsilyl ester

2-nitro-aniline
88-74-4

2-nitro-aniline

3-methyl-2'-nitrobutananilide
150783-30-5

3-methyl-2'-nitrobutananilide

Conditions
ConditionsYield
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
With 4-(trifluoromethyl)benzoic anhydride; silver trifluoromethanesulfonate; titanium tetrachloride In dichloromethane for 20h; Ambient temperature;99%
2-nitro-aniline
88-74-4

2-nitro-aniline

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

bis(2-nitrophenyl)amine
18264-71-6

bis(2-nitrophenyl)amine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h;99%
With potassium carbonate In dimethyl sulfoxide at 120℃; for 36h; Inert atmosphere;95%
With potassium carbonate In dimethyl sulfoxide at 130℃; for 20h; Inert atmosphere; Schlenk technique;94%
2-nitro-aniline
88-74-4

2-nitro-aniline

acetylacetone
123-54-6

acetylacetone

3-(2-(2-nitrophenyl)hydrazineylidene)pentane-2,4-dione
24756-10-3

3-(2-(2-nitrophenyl)hydrazineylidene)pentane-2,4-dione

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite
Stage #2: acetylacetone With sodium hydroxide; sodium acetate In methanol; water at 0 - 20℃; for 1h; Further stages.;
99%
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: acetylacetone With sodium acetate In methanol; water at 20℃;
87%
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium hydroxide; sodium nitrite In water at -0.16℃;
Stage #2: acetylacetone In water at -0.16℃; for 1h;
79%
With hydrogenchloride; sodium acetate; sodium nitrite 1.) water, 0 deg C, 2.) acetone, 6 h; Multistep reaction;
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite at 0℃; for 0.5h;
Stage #2: acetylacetone With sodium acetate In ethanol; water at 0 - 20℃; for 3h; Further stages.;
2-nitro-aniline
88-74-4

2-nitro-aniline

β-naphthol
135-19-3

β-naphthol

1-[(2-nitrophenyl)azo]-2-naphthalenol
6410-09-9

1-[(2-nitrophenyl)azo]-2-naphthalenol

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With sulfuric acid; sodium nitrite In water at 20℃; for 0.333333h;
Stage #2: β-naphthol In water at 20℃; for 2h;
99%
Stage #1: 2-nitro-aniline With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 4.25h;
Stage #2: With aminosulfonic acid In water at 0℃; for 1h;
Stage #3: β-naphthol In ethanol; water at 20℃; for 19.5h;
93%
Stage #1: 2-nitro-aniline With sodium nitrite In water at 20℃; Milling; Green chemistry;
Stage #2: β-naphthol In water at 20℃; for 0.5h; Milling; Green chemistry;
83%
2-nitro-aniline
88-74-4

2-nitro-aniline

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

(E)-methyl 2-nitrocinnamate
39228-29-0

(E)-methyl 2-nitrocinnamate

Conditions
ConditionsYield
With tert.-butylnitrite; methanesulfonic acid; palladium diacetate; methoxybenzene In methanol at 0 - 25℃; for 48h; Reagent/catalyst; Heck Reaction;99%
Stage #1: 2-nitro-aniline With tert.-butylnitrite In methanol at 0℃; for 0.5h;
Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; Heck-Matsuda reaction;
98%
Stage #1: 2-nitro-aniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Heck-Matsuda reaction;
Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; for 48h; Heck-Matsuda reaction;
98%
benzaldehyde
100-52-7

benzaldehyde

2-nitro-aniline
88-74-4

2-nitro-aniline

2-phenyl-1H-benzoimidazole
716-79-0

2-phenyl-1H-benzoimidazole

Conditions
ConditionsYield
With hydrogen In ethyl acetate at 20℃; under 7500.75 Torr; for 20h; Catalytic behavior; Activation energy; Reagent/catalyst; Temperature; Autoclave; Green chemistry;99%
With hydrogen In ethyl acetate at 60℃; under 7500.75 Torr; for 20h; Reagent/catalyst; Solvent; Pressure; Time; Temperature;99%
Stage #1: benzaldehyde; 2-nitro-aniline In 1,4-dioxane; water at 90℃; for 0.0833333h;
Stage #2: With formic acid In 1,4-dioxane; water at 90℃; for 8h; Temperature; Sealed tube;
96%

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