Product Name

  • Name

    6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

  • EINECS
  • CAS No. 36725-28-7
  • Article Data16
  • CAS DataBase
  • Density 1.3 g/cm3
  • Solubility
  • Melting Point 194.0 to 198.0 °C
  • Formula C11H13N3O
  • Boiling Point
  • Molecular Weight 203.244
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 36725-28-7 (6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone)
  • Hazard Symbols
  • Synonyms 6-(4'-Aminophenyl)-4,5-dihydro-5-methylpyridazin-3-one;
  • PSA 71.77000
  • LogP 1.90870

Synthetic route

4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride
120757-13-3

4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid hydrochloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 3h; Heating;98.4%
With hydrazine hydrate In water for 1.5h; Heating;87%
With hydrazine hydrate at 80℃; for 18h;65%
SKF 93741
36725-27-6

SKF 93741

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With hydrogenchloride for 1.25h; Heating;76%
(3S)-4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid

(3S)-4-(4-aminophenyl)-3-methyl-4-oxobutanoic acid

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With hydrazine hydrate In propan-1-ol at 20 - 100℃; for 4h;49%
4-(4-acetamidophenyl)-4-oxobutanoic acid
5473-15-4

4-(4-acetamidophenyl)-4-oxobutanoic acid

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 62 percent / H2O / 1) room temperature, overnight, 2) steam bath, 2 h
2: conc. H2SO4 / 1 h / Heating
3: pyridine
4: H2 / Raney Nickel / methanol / 0.33 h / 1034.3 Torr
5: 90 percent / hydrazine hydrate / ethanol; H2O / 2 h / Heating
6: 76 percent / 1 M aq. HCl / 1.25 h / Heating
View Scheme
N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide
81112-08-5

N-[4-(2-chloro-1-oxopropyl)phenyl]acetamide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) NaH / 1) DMF, room temperature, overnight, 2) DMF, 110 deg C, 3 h
2: 1.) HCl/EtOH, 2.) 6N aq. HCl / 2 h / Heating; 1.) reflux, 2 h, 2.) reflux, 2 h
3: 87 percent / hydrazine hydrate / H2O / 1.5 h / Heating
View Scheme
3-(4-Acetylamino-benzoyl)-but-3-enoic acid methyl ester
120757-16-6

3-(4-Acetylamino-benzoyl)-but-3-enoic acid methyl ester

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2 / Raney Nickel / methanol / 0.33 h / 1034.3 Torr
2: 90 percent / hydrazine hydrate / ethanol; H2O / 2 h / Heating
3: 76 percent / 1 M aq. HCl / 1.25 h / Heating
View Scheme
methyl 3-(4-acetaminobenzoyl)butyrate
120757-17-7

methyl 3-(4-acetaminobenzoyl)butyrate

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / hydrazine hydrate / ethanol; H2O / 2 h / Heating
2: 76 percent / 1 M aq. HCl / 1.25 h / Heating
View Scheme
4-(4-Amino-phenyl)-4-oxo-3-piperidin-1-ylmethyl-butyric acid methyl ester
120757-15-5

4-(4-Amino-phenyl)-4-oxo-3-piperidin-1-ylmethyl-butyric acid methyl ester

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: pyridine
2: H2 / Raney Nickel / methanol / 0.33 h / 1034.3 Torr
3: 90 percent / hydrazine hydrate / ethanol; H2O / 2 h / Heating
4: 76 percent / 1 M aq. HCl / 1.25 h / Heating
View Scheme
2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester
81937-39-5

2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) HCl/EtOH, 2.) 6N aq. HCl / 2 h / Heating; 1.) reflux, 2 h, 2.) reflux, 2 h
2: 87 percent / hydrazine hydrate / H2O / 1.5 h / Heating
View Scheme
Stage #1: 2-ethoxycarbonyl-3-(4-acetamidobenzoyl)butyric acid ethyl ester With sodium hydroxide In water for 4h;
Stage #2: With hydrogenchloride In water at 100℃; for 3h; pH=1; Further stages;		1.8 g
3-(4-acetamidobenzoyl)-4-(N-piperidinyl)butanoic acid
120757-14-4

3-(4-acetamidobenzoyl)-4-(N-piperidinyl)butanoic acid

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: conc. H2SO4 / 1 h / Heating
2: pyridine
3: H2 / Raney Nickel / methanol / 0.33 h / 1034.3 Torr
4: 90 percent / hydrazine hydrate / ethanol; H2O / 2 h / Heating
5: 76 percent / 1 M aq. HCl / 1.25 h / Heating
View Scheme
Acetanilid
103-84-4

Acetanilid

dichloroiodo-benzene

dichloroiodo-benzene

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 61 percent / AlCl3 / CH2Cl2 / Ambient temperature; overnight
2: 1) NaH / 1) DMF, room temperature, overnight, 2) DMF, 110 deg C, 3 h
3: 1.) HCl/EtOH, 2.) 6N aq. HCl / 2 h / Heating; 1.) reflux, 2 h, 2.) reflux, 2 h
4: 87 percent / hydrazine hydrate / H2O / 1.5 h / Heating
View Scheme
(5S)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one
101328-84-1

(5S)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
With sodium hydroxide at 90℃;
N-(4-propionylphenyl)acetamide
16960-49-9

N-(4-propionylphenyl)acetamide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: bromine / chloroform
1.2: 24 h / 20 °C / pH 8
2.1: sodium ethanolate / ethanol / Cooling with ice
2.2: 8.17 h / 35 - 75 °C
3.1: sodium hydroxide / water / 4 h
3.2: 3 h / 100 °C / pH 1
View Scheme
N-(4-(2-bromopropionyl)phenyl)acetamide
63514-63-6

N-(4-(2-bromopropionyl)phenyl)acetamide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium ethanolate / ethanol / Cooling with ice
1.2: 8.17 h / 35 - 75 °C
2.1: sodium hydroxide / water / 4 h
2.2: 3 h / 100 °C / pH 1
View Scheme
Acetanilid
103-84-4

Acetanilid

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: carbon disulfide; aluminum (III) chloride / 50 °C
2.1: bromine / chloroform
2.2: 24 h / 20 °C / pH 8
3.1: sodium ethanolate / ethanol / Cooling with ice
3.2: 8.17 h / 35 - 75 °C
4.1: sodium hydroxide / water / 4 h
4.2: 3 h / 100 °C / pH 1
View Scheme
3-bromopropylamine tert-butylcarbamate
83948-53-2

3-bromopropylamine tert-butylcarbamate

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

tert-butyl {3-[3-(4-aminophenyl)-4-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl]propyl}carbamate

tert-butyl {3-[3-(4-aminophenyl)-4-methyl-6-oxo-5,6-dihydropyridazin-1(4H)-yl]propyl}carbamate

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With sodium hydride In N,N-dimethyl-formamide
Stage #2: 3-bromopropylamine tert-butylcarbamate With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; Cooling with ice;		100%
3-Bromopropionyl chloride
15486-96-1

3-Bromopropionyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-<4-(3-bromopropionamido)phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone
111794-34-4

6-<4-(3-bromopropionamido)phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Conditions
ConditionsYield
In acetonitrile for 3h; Heating;99%
With sodium hydrogencarbonate In dichloromethane
C9H6ClNO4

C9H6ClNO4

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)-6-nitrobenzo[d][1,3]dioxole-5-carboxamide

N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)-6-nitrobenzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;88.7%
6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

C22H23N7O2

C22H23N7O2

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 0℃; for 1h;86%
3-bromopropanol methyl ether
36865-41-5

3-bromopropanol methyl ether

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-aminophenyl)-2-(3-methoxypropyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

6-(4-aminophenyl)-2-(3-methoxypropyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h;
Stage #2: 3-bromopropanol methyl ether In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;		85%
2,4,5-trifluoro-3-methylbenzamide
112822-86-3

2,4,5-trifluoro-3-methylbenzamide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

2,4,5-trifluoro-3-methyl-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

2,4,5-trifluoro-3-methyl-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;84.2%
3-methyl-4-nitro-benzoyl chloride
35675-46-8

3-methyl-4-nitro-benzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

3-methyl-4-nitro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

3-methyl-4-nitro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;83.2%
6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-hydrazinophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one hydrochloride

6-(4-hydrazinophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one hydrochloride

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With hydrogenchloride; sodium nitrite at 0℃; for 0.5h;
Stage #2: With hydrogenchloride; tin(ll) chloride at 0℃; for 1h;		83%
4-chloro-6-methoxy-2-methylquinoline
50593-73-2

4-chloro-6-methoxy-2-methylquinoline

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

C22H22N4O2

C22H22N4O2

Conditions
ConditionsYield
In butan-1-ol for 4h; Heating;83%
5-chloro-2-nitrobenzoyl chloride
41994-44-9

5-chloro-2-nitrobenzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

5-chloro-2-nitro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

5-chloro-2-nitro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;76.3%
ethyl iodide
75-03-6

ethyl iodide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-aminophenyl)-2-ethyl-5-methyl-4,5-dihydropyridazin-3(2H)-one

6-(4-aminophenyl)-2-ethyl-5-methyl-4,5-dihydropyridazin-3(2H)-one

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; Reagent/catalyst;		76%
N-carbobenzoxy-β-alanine-p-nitrophenyl ester
3642-91-9

N-carbobenzoxy-β-alanine-p-nitrophenyl ester

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-<4-<3-<(benzyloxycarbonyl)amino>propionamido>phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone
111794-60-6

6-<4-<3-<(benzyloxycarbonyl)amino>propionamido>phenyl>-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Conditions
ConditionsYield
In N,N-dimethyl-formamide73%
Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-aminophenyl)-2-cyclopentyl-5-methyl-4,5-dihydropyridazin-3(2H)-one

6-(4-aminophenyl)-2-cyclopentyl-5-methyl-4,5-dihydropyridazin-3(2H)-one

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h;
Stage #2: Cyclopentyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;		71%
4-chloro-2-nitro-benzoyl chloride
41995-04-4

4-chloro-2-nitro-benzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

4-chloro-2-nitro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

4-chloro-2-nitro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;65.7%
2,4-dichloro-5-fluorobenzoyl chloride
86393-34-2

2,4-dichloro-5-fluorobenzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

2,4-dichloro-5-fluoro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

2,4-dichloro-5-fluoro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;65.4%
dimethyl N-cyanodithioiminocarbonate
10191-60-3

dimethyl N-cyanodithioiminocarbonate

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-<4-(N'-cyano-S-methylisothioureido)phenyl>-5-methyl-4,5-dihydropyridazin-3(2H)-one
99591-85-2, 123466-25-1

6-<4-(N'-cyano-S-methylisothioureido)phenyl>-5-methyl-4,5-dihydropyridazin-3(2H)-one

Conditions
ConditionsYield
With pyridine for 3.5h; Heating;65%
3-Chloro-2,4,5-trifluorobenzoyl chloride
101513-78-4

3-Chloro-2,4,5-trifluorobenzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

3-chloro-2,4,5-trifluoro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

3-chloro-2,4,5-trifluoro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;63.8%
di(succinimido) carbonate
74124-79-1

di(succinimido) carbonate

2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrogen chloride
6000-50-6

2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrogen chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

N-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

N-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl]-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide

Conditions
ConditionsYield
Stage #1: di(succinimido) carbonate; 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With dmap In tetrahydrofuran at 20℃; for 72h;
Stage #2: 2,3-dihydro-1H-pyrrolo[3,4-c]pyridine dihydrogen chloride With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide		63%
...Expand
1,3-Dihydro-isobenzofuran-5-carbonyl chloride
153967-93-2

1,3-Dihydro-isobenzofuran-5-carbonyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzo[d][1,3]dioxole-5-carboxamide

N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzo[d][1,3]dioxole-5-carboxamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;60.5%
4-chloro-2,6-dimethylquinoline
6270-08-2

4-chloro-2,6-dimethylquinoline

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

C22H22N4O

C22H22N4O

Conditions
ConditionsYield
In butan-1-ol for 4h; Heating;60%
pyruvic acid methyl ester
600-22-6

pyruvic acid methyl ester

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

methyl 2-(2-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)hydrazono)propanoate

methyl 2-(2-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)hydrazono)propanoate

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h;
Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In water at 0℃; for 0.166667h;
Stage #3: pyruvic acid methyl ester In water at 20℃; for 0.5h;		60%
2,3-dichlorobenzoyl chloride
2905-60-4

2,3-dichlorobenzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

2,3-dichloro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

2,3-dichloro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;59.5%
1-trimethylsiloxy-3-bromo-propane
34714-04-0

1-trimethylsiloxy-3-bromo-propane

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-aminophenyl)-5-methyl-2-{3-[(trimethylsilyl)oxy]propyl}-4,5-dihydropyridazin-3(2H)-one

6-(4-aminophenyl)-5-methyl-2-{3-[(trimethylsilyl)oxy]propyl}-4,5-dihydropyridazin-3(2H)-one

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h;
Stage #2: 1-trimethylsiloxy-3-bromo-propane In N,N-dimethyl-formamide; mineral oil at 20℃;		58%
6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

5-methyl-6-phenyl-4,5-dihydro-2H-pyridazin-3-one
110766-33-1

5-methyl-6-phenyl-4,5-dihydro-2H-pyridazin-3-one

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With hydrogenchloride; sodium nitrite In water at 0℃; for 0.333333h;
Stage #2: With hypophosphorous acid In water		55%
2-chloropropionyl chloride
7623-09-8

2-chloropropionyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

amipizone
69635-63-8

amipizone

Conditions
ConditionsYield
In tetrahydrofuran for 6h; Heating;54%
2-(tert-butyldimethylsilyloxy)ethyl bromide
86864-60-0

2-(tert-butyldimethylsilyloxy)ethyl bromide

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

6-(4-aminophenyl)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

6-(4-aminophenyl)-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one

Conditions
ConditionsYield
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h;
Stage #2: With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil for 0.25h;
Stage #3: 2-(tert-butyldimethylsilyloxy)ethyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 14h;		53%
Stage #1: 6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h;
Stage #2: 2-(tert-butyldimethylsilyloxy)ethyl bromide With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 14h;
3-chlorobutanoyl chloride
1951-11-7

3-chlorobutanoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

3-Chloro-N-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-butyramide
85221-85-8

3-Chloro-N-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-butyramide

Conditions
ConditionsYield
In tetrahydrofuran for 6h; Heating;52%
2,3,4,5-tetrafluorobenzoyl chloride
94695-48-4

2,3,4,5-tetrafluorobenzoyl chloride

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone
36725-28-7

6-(4-aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone

2,4,3,5-tetrafluoro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

2,4,3,5-tetrafluoro-N-(4-(4-methyl-6-oxo-1,4,5,6-tetrahydropyridazin-3-yl)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃;51.2%

6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone Specification

The IUPAC name of 6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone is 3-(4-aminophenyl)-4-methyl-4,5-dihydro-1H-pyridazin-6-one. With the CAS registry number 36725-28-7, it is also named as 3(2H)-Pyridazinone, 6-(4-aminophenyl)-4,5-dihydro-5-methyl-. The product's category is intermediate of levosimendan. In addition, its molecular formula is C11H13N3O and molecular weight is 203.24.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.75; (4)ACD/LogD (pH 7.4): -0.75; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 9.28; (8)ACD/KOC (pH 7.4): 9.33; (9)H bond acceptors: 4; (10)H bond donors: 3; (11)Freely Rotating Bonds: 2; (12)Polar Surface Area: 35.91 Å2; (13)Index of Refraction: 1.652; (14) Molar Refractivity: 56.82 cm3; (15)Molar Volume: 155.2 cm3; (16)Polarizability: 22.52×10-24cm3; (17)Surface Tension: 50.6 dyne/cm; (18)Density: 1.3 g/cm3.

Preparation of 6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone: this chemical can be prepared by 3-(4-Aminobenzoyl)butanoic acid hydrochloride.



This reaction needs Hydrazine hydrate and H2O by heating. The reaction time is 1.5 hours. The yield is 87 %.

Uses of 6-(4-Aminophenyl)-4,5-dihydro-5-methyl-3(2H)-pyridazinone: it can react with 3-Bromo-propionyl chloride to get 6-[4-(3-Bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone.



This reaction needs Acetonitrile by heating for 3 hours. The yield is 99 %.

People can use the following data to convert to the molecule structure.
(1)SMILES:O=C2N/N=C(/c1ccc(N)cc1)C(C)C2
(2)InChI:InChI=1/C11H13N3O/c1-7-6-10(15)13-14-11(7)8-2-4-9(12)5-3-8/h2-5,7H,6,12H2,1H3,(H,13,15)
(3)InChIKey:GDMRFHZLKNYRRO-UHFFFAOYAA
(4)Std. InChI:InChI=1S/C11H13N3O/c1-7-6-10(15)13-14-11(7)8-2-4-9(12)5-3-8/h2-5,7H,6,12H2,1H3,(H,13,15)
(5)Std. InChIKey:GDMRFHZLKNYRRO-UHFFFAOYSA-N

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View