2-methyl-5-pyridylacetylene
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With sulfuric acid In toluene at 80℃; for 3h; Inert atmosphere; | 92% |
With sulfuric acid In toluene at 50℃; | 91% |
Stage #1: 2-methyl-5-pyridylacetylene With sulfuric acid In toluene at 50℃; Stage #2: With sodium hydrogencarbonate In toluene | 91% |
Methyl 6-methylnicotinate
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: Methyl 6-methylnicotinate With sodium hydride In ethyl acetate; N,N-dimethyl-formamide; toluene at 80℃; for 10h; Stage #2: With sulfuric acid In water at 110℃; for 2h; Stage #3: With potassium carbonate In water pH=9; | 65% |
Multi-step reaction with 2 steps 1: NaH / dimethylformamide; toluene / 2.5 h / 80 °C 2: 10percent aq. H2SO4 / 2 h / Heating View Scheme |
Methyl 6-methylnicotinate
ethyl acetate
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: Methyl 6-methylnicotinate; ethyl acetate With sodium hydride In N,N-dimethyl-formamide; toluene at 80℃; for 10h; Stage #2: With sulfuric acid In water at 110℃; for 2h; Stage #3: With potassium carbonate In water pH=9; | 65% |
Stage #1: Methyl 6-methylnicotinate; ethyl acetate With lithium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide at -50 - 20℃; for 1h; Stage #2: With sulfuric acid In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 4h; Reflux; |
1-amino-1-buten-3-one
A
1-(6-methyl-pyridin-3-yl)-ethanone
B
1-(4-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
for 15h; heating on water bath; | A 47% B n/a |
for 15h; heating on water bath; |
5-ethyl-2-methyl-pyridine
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: 5-ethyl-2-methyl-pyridine With sulfuric acid; acetic anhydride; acetic acid Stage #2: With chromium(VI) oxide at 10 - 20℃; Stage #3: With sodium carbonate In water | 31% |
Stage #1: 5-ethyl-2-methyl-pyridine With chromium(VI) oxide; sulfuric acid; acetic anhydride In acetic acid at 20 - 30℃; for 24h; Stage #2: With sodium carbonate In water |
A
1-(6-methyl-pyridin-3-yl)-ethanone
B
hydrogen cyanide
Conditions | Yield |
---|---|
beim Aufbewahren an der Luft; |
acetylacetaldehyde dimethyl acetal
1-amino-1-buten-3-one
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid |
1-amino-1-buten-3-one
(E)-4-chloro-3-buten-2-one
1-(6-methyl-pyridin-3-yl)-ethanone
ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With sulfuric acid for 2h; Heating; Yield given; | |
With sulfuric acid; water for 2h; Product distribution / selectivity; Heating / reflux; |
methylmagnesium chloride
N-methoxy-N-methyl-6-methylnicotinamide
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
In tetrahydrofuran Substitution; |
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With chromic acid; acetic acid |
3-(1-hydroxyethyl)-6-methylpyridine
acetic acid
1-(6-methyl-pyridin-3-yl)-ethanone
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With ammonium acetate; diethyl ether; acetic acid | |
With ammonium acetate; diethyl ether; acetic acid |
6-methyl-nicotinoyl chloride
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: tetrahydrofuran View Scheme |
ethyl 6-methylnicotinate
ethyl acetate
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: ethyl 6-methylnicotinate; ethyl acetate With sodium hydride In N,N-dimethyl-formamide; toluene at 80℃; for 2.5h; Stage #2: With sulfuric acid; water for 2h; Heating / reflux; Stage #3: With water; potassium carbonate at 0℃; Product distribution / selectivity; |
methylmagnesium bromide
N-methoxy-N-methyl-6-methylnicotinamide
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at 0 - 20℃; for 16h; |
Methyl 6-methylnicotinate
N,N-dimethyl-formamide
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: Methyl 6-methylnicotinate; N,N-dimethyl-formamide With lithium hexamethyldisilazane In tetrahydrofuran; ethyl acetate at -50 - 20℃; for 1h; Stage #2: With sulfuric acid In tetrahydrofuran; ethyl acetate at 0℃; for 4h; Reflux; |
(6-methylpyridin-3-yl)trifluoromethanesulfonate
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: piperidine; Tri(p-tolyl)phosphine / palladium diacetate / toluene; 1-methyl-pyrrolidin-2-one / Inert atmosphere 1.2: 40 °C 1.3: 2 h / Reflux 2.1: sulfuric acid / toluene / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: piperidine / palladium diacetate; Tri(p-tolyl)phosphine / toluene; 1-methyl-pyrrolidin-2-one / 40 °C / Inert atmosphere 1.2: 2 h / Reflux 2.1: sulfuric acid / toluene / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: piperidine; palladium diacetate; Tri(p-tolyl)phosphine / toluene; 1-methyl-pyrrolidin-2-one / 16 h / 40 °C / Inert atmosphere 2: sodium hydroxide / toluene / 2 h / Inert atmosphere; Reflux 3: sulfuric acid / toluene / 3 h / 80 °C / Inert atmosphere View Scheme |
5-Hydroxy-2-methylpyridine
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 1.5 h / 0 °C 2.1: piperidine; Tri(p-tolyl)phosphine / palladium diacetate / toluene; 1-methyl-pyrrolidin-2-one / Inert atmosphere 2.2: 40 °C 2.3: 2 h / Reflux 3.1: sulfuric acid / toluene / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 1.5 h / 0 °C 2.1: piperidine / palladium diacetate; Tri(p-tolyl)phosphine / toluene; 1-methyl-pyrrolidin-2-one / 40 °C / Inert atmosphere 2.2: 2 h / Reflux 3.1: sulfuric acid / toluene / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere 2: piperidine; palladium diacetate; Tri(p-tolyl)phosphine / toluene; 1-methyl-pyrrolidin-2-one / 16 h / 40 °C / Inert atmosphere 3: sodium hydroxide / toluene / 2 h / Inert atmosphere; Reflux 4: sulfuric acid / toluene / 3 h / 80 °C / Inert atmosphere View Scheme |
2-methyl-4-(6-methylpyridin-3-yl)but-3-yn-2-ol
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / toluene / 2 h / Inert atmosphere; Reflux 2: sulfuric acid / toluene / 3 h / 80 °C / Inert atmosphere View Scheme |
5-bromo-2-methylpyridine
1-(trimethylsilyl)ethanone
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dichloro-ethane at 75℃; for 6h; Inert atmosphere; Sealed tube; | 73 %Spectr. |
6-methylnicotinic acid
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C 2: tetrahydrofuran; hexane / 16 h / 0 - 20 °C View Scheme |
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With chloroform-d1; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 22℃; for 0.5h; | 99% |
1-(6-methyl-pyridin-3-yl)-ethanone
oxalic acid diethyl ester
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanone With lithium hexamethyldisilazane In tetrahydrofuran for 1h; Cooling; Stage #2: oxalic acid diethyl ester In tetrahydrofuran at 20℃; for 4h; Cooling; | 94% |
morpholine
1-(6-methyl-pyridin-3-yl)-ethanone
4-[(6-methyl-pyridin-3-yl)-thioacetyl]-morpholine
Conditions | Yield |
---|---|
With sulfur for 17h; Reflux; | 93.3% |
With sulfur In water; ethyl acetate at 110℃; for 7h; | |
With sulfur at 110℃; for 7h; |
1-(6-methyl-pyridin-3-yl)-ethanone
ethylene glycol
3-(2-methyl-1,3-dioxolan-2-yl)-6-methylpyridine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 8h; Heating; | 92% |
1-(6-methyl-pyridin-3-yl)-ethanone
4-bromoohenyl methyl sulfone
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
Conditions | Yield |
---|---|
With potassium phosphate; palladium(II) acetylacetonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1-methyl-pyrrolidin-2-one at 100℃; for 18h; Product distribution / selectivity; Inert atmosphere; | 91% |
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene for 5h; Concentration; Inert atmosphere; Reflux; | 75% |
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene for 4h; Concentration; Inert atmosphere; Reflux; | 75% |
1-(6-methyl-pyridin-3-yl)-ethanone
3-(1-hydroxyethyl)-6-methylpyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0℃; for 1.5h; | 90% |
With sodium tetrahydroborate In ethanol for 0.5h; | 76% |
With water; platinum Hydrogenation; |
1-(6-methyl-pyridin-3-yl)-ethanone
N,N-dimethyl-formamide dimethyl acetal
Conditions | Yield |
---|---|
for 18h; Heating / reflux; | 90% |
morpholine
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
Stage #1: morpholine; 1-(6-methyl-pyridin-3-yl)-ethanone With sulfur for 16h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water | 87.9% |
1-(6-methyl-pyridin-3-yl)-ethanone
1-(6-methyl-[3]pyridyl)-ethanone oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol at 25℃; for 7h; | 85% |
1-(6-methyl-pyridin-3-yl)-ethanone
C8H13NO
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C40H38I2N4(2+)*2CF3O3S(1-) In dichloromethane at 20℃; for 48h; Inert atmosphere; | 83% |
1-(6-methyl-pyridin-3-yl)-ethanone
6-methylnicotinic acid
Conditions | Yield |
---|---|
With nitric acid for 5h; Heating; | 75.4% |
With nitric acid |
1-(6-methyl-pyridin-3-yl)-ethanone
α-bromoacetophenone
5-Acetyl-2-methyl-1-(2-oxo-2-phenyl-ethyl)-pyridinium; bromide
Conditions | Yield |
---|---|
In butanone for 15h; Heating; | 72% |
1-(6-methyl-pyridin-3-yl)-ethanone
4-bromoohenyl methyl sulfone
1-(6-methylpyridin-3-yl)-2-[(4-methylsulfonyl)-phenyl]-ethanone hydrochloride
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanone; 4-bromoohenyl methyl sulfone With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 60℃; for 3h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water; toluene at 25℃; | 70% |
Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanone; 4-bromoohenyl methyl sulfone With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene for 3h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride Reflux; | 70% |
1-(6-methyl-pyridin-3-yl)-ethanone
4-bromoohenyl methyl sulfone
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanone; 4-bromoohenyl methyl sulfone With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 60℃; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water; toluene Reflux; | 70% |
1-(6-methyl-pyridin-3-yl)-ethanone
4-chlorophenyl methyl sulfone
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
Conditions | Yield |
---|---|
With palladium(II) acetylacetonate; potassium phosphate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In dimethyl sulfoxide at 150℃; for 16h; Inert atmosphere; | 69% |
1-(6-methyl-pyridin-3-yl)-ethanone
ethyl Pentafluoropropionate
Conditions | Yield |
---|---|
With lithium hydride In tetrahydrofuran Claisen Condensation; | 69% |
1-(6-methyl-pyridin-3-yl)-ethanone
cyclohexylhydrazine
Conditions | Yield |
---|---|
In ethanol at 90℃; for 5h; | 62% |
1-(6-methyl-pyridin-3-yl)-ethanone
(S)-2-methylpropane-2-sulfinamide
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanone; (S)-2-methylpropane-2-sulfinamide In tetrahydrofuran at 80℃; for 2h; Stage #2: With L-Selectride In tetrahydrofuran at -78 - -70℃; for 1.5h; | 34% |
Dimethyl oxalate
1-(6-methyl-pyridin-3-yl)-ethanone
2-hydroxy-4-(6-methylpyridin-3-yl)-4-oxo-but-2-enoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: Dimethyl oxalate With sodium methylate In methanol for 0.25h; Claisen condensation; Stage #2: 1-(6-methyl-pyridin-3-yl)-ethanone In methanol at 30℃; for 0.0833333h; Claisen condensation; Microwave irradiation; | 16% |
1-(6-methyl-pyridin-3-yl)-ethanone
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 12h; | 16% |
1-(6-methyl-pyridin-3-yl)-ethanone
2-(6-methyl-pyridin-3-yl)-acetamide
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-pyridin-3-yl)-ethanone With pyridine; ammonia for 0.5h; Stage #2: With sulfur at 160℃; for 17h; | 15% |
furfural
1-(6-methyl-pyridin-3-yl)-ethanone
3-furan-2-yl-1-(6-methyl-pyridin-3-yl)-propenone
1-(6-methyl-pyridin-3-yl)-ethanone
methyl magnesium iodide
2-(6-methylpyridin-3-yl)propan-2-ol
Conditions | Yield |
---|---|
With diethyl ether |
1-(6-methyl-pyridin-3-yl)-ethanone
hydrogen cyanide
1-(6-methyl-pyridin-3-yl)-ethanone
hydrogen cyanide
Molecular Structure of 5-Acetyl-2-methylpyridine (CAS NO.36357-38-7):
IUPAC Name: 1-(6-methylpyridin-3-yl)ethanone
Empirical Formula: C8H9NO
Molecular Weight: 135.1632
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 29.96 Å2
Index of Refraction: 1.512
Molar Refractivity: 39.19 cm3
Molar Volume: 130.4 cm3
Surface Tension: 38.1 dyne/cm
Density: 1.036 g/cm3
Flash Point: 103.9 °C
Enthalpy of Vaporization: 47.03 kJ/mol
Boiling Point: 233.6 °C at 760 mmHg
Vapour Pressure: 0.0553 mmHg at 25°C
EINECS: 252-995-8
Product Categories: Pyridine; Heterocyclic Compounds; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides; Pyridines
InChI
InChI=1/C8H9NO/c1-6-3-4-8(5-9-6)7(2)10/h3-5H,1-2H3
Smiles
n1cc(C(=O)C)ccc1C
5-Acetyl-2-methylpyridine , with CAS number of 36357-38-7, can be called 1-(6-methylpyridin-3-yl)ethan-1-one ; 1-(6-Methyl-3-pyridinyl)-ethanone ; 2-Methyl-5-acetylpyridine ; 5-Acetyl-2-picoline ; Methyl 6-Methyl-3-pyridyl Ketone ; Ethanone, 1-(6-methyl-3-pyridinyl)- ; 5-Acetyl-2-methylpyridine . It is a pale-yellow oil.
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