Conditions | Yield |
---|---|
With 5% active carbon-supported ruthenium; hydrogen at 30℃; under 3750.38 Torr; for 4h; Temperature; Pressure; Reagent/catalyst; | 98.2% |
With palladium on activated charcoal; hydrogen In water at 10℃; under 22502.3 Torr; Pressure; Temperature; Solvent; Reagent/catalyst; | 89.7% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethyl acetate at 60℃; for 0.25h; Ring cleavage; | 90% |
Conditions | Yield |
---|---|
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water for 1h; Stage #2: With sodium sulfite at 80℃; for 2.5h; Stage #3: With hydrogenchloride In water at 95℃; for 2h; | 88.3% |
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 5℃; Stage #2: With sodium carbonate; sodium sulfite In water at 5 - 70℃; | 65.4% |
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite Stage #2: With tin(ll) chloride | 64.3% |
Conditions | Yield |
---|---|
Stage #1: bromochlorobenzene With hydrazine hydrate; copper(II) sulfate; cobalt(II) chloride In propylene glycol at 152℃; for 10h; Stage #2: With hydrogenchloride In water Reagent/catalyst; Temperature; Solvent; | 88.1% |
Stage #1: bromochlorobenzene With 2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin; hydrazine hydrate; copper(I) bromide In propylene glycol; water at 172℃; for 5h; Stage #2: With hydrogenchloride In water at 70℃; pH=1.8; Reagent/catalyst; Solvent; Temperature; Time; pH-value; | 86.3% |
Stage #1: bromochlorobenzene With potassium phosphate; copper(l) iodide; N,N′-bis(2,6-dimethylphenyl)oxalamide; cetyltrimethylammonim bromide In water at 80℃; for 0.25h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With hydrazine hydrate In water at 80℃; Inert atmosphere; Schlenk technique; Sealed tube; Stage #3: With hydrogenchloride In water pH=3 - 4; Inert atmosphere; Schlenk technique; Sealed tube; | 85% |
Stage #1: bromochlorobenzene With potassium phosphate; N,N'-bis(2,5-dimethylpyrrol-1-yl)oxalamide; cetyltrimethylammonim bromide; copper(I) bromide In water at 110℃; for 0.166667h; Sealed tube; Inert atmosphere; Stage #2: With hydrazine hydrate In water at 110℃; for 1.5h; Sealed tube; Inert atmosphere; Stage #3: With hydrogenchloride In dichloromethane; water | 80% |
ethanol
4-chloro-3-(4-chlorophenyl)sydnone
A
4-chlorophenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride |
(3R,4S)-4-hydroxy-2-oxotetrahydrofuran-3-yl 2-(2-(4-chlorophenyl)hydrazinyl)-2-oxoacetate
4-chlorophenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; methanol at 90℃; for 2h; |
4-Chlor-phenylnitrosamin
4-chlorophenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride In water at 0℃; |
3-methyl-butan-2-one
4-chlorophenylhydrazine hydrochloride
5-chloro-2,3,3-trimethyl-3H-indole
Conditions | Yield |
---|---|
With sulfuric acid In water at 100℃; for 0.166667h; Reagent/catalyst; Temperature; Microwave irradiation; Green chemistry; | 100% |
With sulfuric acid In water at 100℃; for 0.166667h; Wavelength; Microwave irradiation; Inert atmosphere; Green chemistry; | 100% |
With perchloric acid In ethanol Fischer indolization; Heating; | 88% |
Conditions | Yield |
---|---|
at 250℃; for 0.0166667h; Fischer indole synthesis; | 100% |
4-chlorophenylhydrazine hydrochloride
cyclopentanone
7-chloro-1,2,3,4-tetrahydrocyclopenta[b]indole
Conditions | Yield |
---|---|
at 250℃; for 0.0166667h; Fischer indole synthesis; | 100% |
With acetic acid Fischer Indole Synthesis; Reflux; | 10% |
ethyl 4-oxocyclohexane-1-carboxylate
4-chlorophenylhydrazine hydrochloride
ethyl 6-chloro-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate
Conditions | Yield |
---|---|
In acetic acid at 20℃; for 17h; Heating / reflux; | 100% |
With hydrogenchloride In ethanol; water Fischer Indole Synthesis; Reflux; | 64% |
4-chlorophenylhydrazine hydrochloride
1,1,1-trifluoro-4-(4-methoxyphenyl)but-3-yn-2-one
Conditions | Yield |
---|---|
Stage #1: 4-chlorophenylhydrazine hydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene Stage #2: 1,1,1-trifluoro-4-(4-methoxyphenyl)but-3-yn-2-one at 20℃; for 24h; regioselective reaction; | 100% |
4-chlorophenylhydrazine hydrochloride
1-phenyl-propan-1-one
5-chloro-3-methyl-2-phenyl-1H-indole
Conditions | Yield |
---|---|
at 250℃; for 0.0166667h; Fischer indole synthesis; | 99% |
With toluene-4-sulfonic acid for 0.0833333h; Fischer indole synthesis; Microwave irradiation; neat (no solvent); | 95% |
With acetic acid at 120℃; Inert atmosphere; | |
With acetic acid at 120℃; Inert atmosphere; |
4H-spiro[cyclohexane-1,3'-indole]-2’,4(1‘H)-dione
4-chlorophenylhydrazine hydrochloride
6-chloro-1,2,4,9-tetrahydrospiro[carbazole-3,3'indolin]-2'-one
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine In ethanol at 80℃; for 3h; Fischer Indole Synthesis; | 99% |
4-chlorophenylhydrazine hydrochloride
(E)-5-(2-Dimethylamino-vinyl)-1-phenyl-1H-tetrazol
Conditions | Yield |
---|---|
With water; acetic acid In methanol for 0.0833333h; Heating; | 98% |
4-chlorophenylhydrazine hydrochloride
7-chloro-2-(2,4-dichlorophenyl)-3,4-dihydro-2H-thieno[3,2-b]indole
Conditions | Yield |
---|---|
In ethanol at 90℃; under 1500.15 Torr; for 0.0666667h; Fischer indole synthesis; Microwave irradiation; | 98% |
4-chlorophenylhydrazine hydrochloride
2,6-dichloro-pyrimidine carbaldehyde
4,6-dichloro-5-((2-(4-chlorophenyl)hydrazono)methyl)pyrimidine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 65℃; for 1h; Temperature; Reagent/catalyst; Inert atmosphere; | 98% |
4-chlorophenylhydrazine hydrochloride
1-benzyl-4-(1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
In water for 1h; Solvent; Reflux; Green chemistry; | 98% |
4-chlorophenylhydrazine hydrochloride
1-benzyl-4-(1-(4-chlorophenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
In water for 1.5h; Solvent; Reflux; Green chemistry; | 98% |
2-oxo-propionic acid ethyl ester
4-chlorophenylhydrazine hydrochloride
2-[(4-chlorophenyl)-hydrazono]-propionic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-chlorophenylhydrazine hydrochloride In ethanol at 50℃; for 1h; Inert atmosphere; Stage #2: 2-oxo-propionic acid ethyl ester In ethanol at 20 - 50℃; for 4h; Inert atmosphere; | 98% |
In ethanol; water at 80℃; for 3h; Fischer Indole Synthesis; Green chemistry; | 91% |
In ethanol Reflux; |
1-(2-fluoro-5-nitrophenyl)ethanone
4-chlorophenylhydrazine hydrochloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere; | 98% |
4-chlorophenylhydrazine hydrochloride
1-benzyl-4-(5-(4-bromophenyl)-1-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl)-5-methyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
In water for 1.5h; Solvent; Reflux; Green chemistry; | 97% |
4-chlorophenylhydrazine hydrochloride
2-nitrophenylmethyl bromide
2-[(N-4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]-1-nitrobenzene
Conditions | Yield |
---|---|
In ethanol at 20℃; Solvent; | 96.3% |
4-chlorophenylhydrazine hydrochloride
(E)-4-(1-Formyl-naphthalen-2-yloxy)-but-2-enenitrile
Conditions | Yield |
---|---|
In ethanol Ambient temperature; | A n/a B 96% C n/a |
4-chlorophenylhydrazine hydrochloride
2-Methylcyclohexanone
A
6-chloro-1,2,3,4-tetrahydro-1-methylcarbazole
B
6-chloro-2,3,4,4a-tetrahydro-4a-methyl-1H-carbazole
Conditions | Yield |
---|---|
In acetic acid for 0.25h; Heating; | A 4% B 96% |
4-chlorophenylhydrazine hydrochloride
A
C19H17ClN2O2
B
C19H17ClN2O2
Conditions | Yield |
---|---|
With acetic acid In methanol at 30℃; for 1h; | A n/a B 96% |
Conditions | Yield |
---|---|
With sodium acetate In ethanol at 80℃; for 0.0833333h; Microwave irradiation; air-cooling; | 96% |
In ethanol for 5h; Reflux; | 87% |
4-chlorophenylhydrazine hydrochloride
chloroformic acid ethyl ester
ethyl 2-(4-chlorophenyl)hydrazinecarboxylate
Conditions | Yield |
---|---|
With pyridine In acetonitrile at 0 - 20℃; | 96% |
With pyridine In acetonitrile at 0 - 20℃; for 1h; |
4-chlorophenylhydrazine hydrochloride
indole-2,3-dione
(3Z)-1H-indole-2,3-dione 3-[(4-chlorophenyl)hydrazone]
Conditions | Yield |
---|---|
In methanol at 20℃; | 96% |
3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(p-tolyl)-2-propyn-1-one
4-chlorophenylhydrazine hydrochloride
8-(1-(4-chlorophenyl)-5-(p-tolyl)-1H-pyrazol-3-yl)-1,4-dioxaspiro[4.5]decan-8-ol
Conditions | Yield |
---|---|
Stage #1: 4-chlorophenylhydrazine hydrochloride With triethylamine In ethanol at 20℃; for 0.5h; Stage #2: 3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(p-tolyl)-2-propyn-1-one In ethanol at 20℃; for 14h; | 96% |
Stage #1: 4-chlorophenylhydrazine hydrochloride With triethylamine In ethanol at 20℃; for 0.5h; Stage #2: 3-(8-hydroxy-1,4-dioxaspiro[4.5]decan-8-yl)-1-(p-tolyl)-2-propyn-1-one In ethanol at 20℃; for 14h; | 96% |
4-chlorophenylhydrazine hydrochloride
Conditions | Yield |
---|---|
In water at 130 - 140℃; Microwave irradiation; | 96% |
3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one
4-chlorophenylhydrazine hydrochloride
dehydroacetic acid (4-chlorophenyl)hydrazone
Conditions | Yield |
---|---|
With sodium acetate In methanol for 15h; Ambient temperature; | 95% |
4-chlorophenylhydrazine hydrochloride
2-((2-(4-chlorophenyl)hydrazinyl)methylene)-5,5-dimethylcyclohexane-1,3-dione
Conditions | Yield |
---|---|
In water at 80 - 90℃; Condensation; | 95% |
N-(5-benzoyl-6-methyl-2-oxo-2H-pyran-3-yl)benzamide
4-chlorophenylhydrazine hydrochloride
Conditions | Yield |
---|---|
With pyridine In ethanol for 1.33333h; Heating; | 95% |
4-chlorophenylhydrazine hydrochloride
cyclohexanone
6-chloro-1,2,3,4-tetrahydrocarbazole
Conditions | Yield |
---|---|
With 1,3-bis(3-sulfopropyl)-1H-imidazol-3-ium trifluoromethanesulfonate In water at 100℃; for 0.333333h; Fischer Indole Synthesis; Microwave irradiation; Green chemistry; | 95% |
With acetic acid for 8h; Reflux; | 92% |
at 250℃; for 0.0166667h; Fischer indole synthesis; | 91% |
4-chlorophenylhydrazine hydrochloride
ethyl acetoacetate
1-(4-chlorophenyl)-3-methyl-2-pyrazolin-5-one
Conditions | Yield |
---|---|
With sodium acetate; acetic acid at 20℃; for 24h; | 95% |
With sodium acetate In acetic acid Reflux; | 80% |
With triethylamine In ethanol for 19h; Heating; | 60% |
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