4-chloro-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; | 88% |
acetylacetaldehyde dimethyl acetal
cyanoacetic acid amide
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With piperdinium acetate In water for 24h; Reflux; | 87.4% |
With piperidinyl acetate at 80℃; for 24h; | 80% |
With piperdinium acetate at 80℃; for 24h; | 73% |
3-oxo-butyraldehyde; sodium enolate
cyanoacetic acid amide
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With piperdinium acetate at 100℃; for 2h; | 75% |
acetone
cyanoacetic acid amide
formic acid ethyl ester
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
Stage #1: acetone; formic acid ethyl ester With sodium methylate In tetrahydrofuran at 0 - 20℃; for 2h; Stage #2: cyanoacetic acid amide With piperidine; acetic acid In tetrahydrofuran; water for 2h; Reflux; | 61% |
Stage #1: acetone; formic acid ethyl ester With sodium In diethyl ether at 20℃; Cooling with ice; Stage #2: cyanoacetic acid amide In diethyl ether at 20℃; for 0.1h; Stage #3: With piperidine; water; acetic acid In diethyl ether for 2h; Reflux; | 58% |
Stage #1: acetone; formic acid ethyl ester With sodium methylate In diethyl ether at 0 - 20℃; for 2h; Stage #2: cyanoacetic acid amide With piperdinium acetate In water for 2h; Heating / reflux; | 49% |
3-oxo-butyraldehyde; sodium (Z)-1-enolate
cyanoacetic acid amide
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With piperdinium acetate In water for 0.166667h; Cycloaddition; Heating; | 58% |
5-cyano-2-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With copper In quinoline for 3h; Heating; | 57% |
1-cyanoformamide
acetylacetaldehyde dimethyl acetal
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With piperdinium acetate for 24h; pH=9.5; Heating; | 57% |
piperidine
cyanoacetic acid amide
formic acid ethyl ester
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With sodium methylate; piperdinium acetate; acetic acid In diethyl ether; water; acetone | 49% |
With sodium methylate; piperdinium acetate; acetic acid In diethyl ether; water; acetone | 49% |
With sodium methylate; piperdinium acetate; acetic acid In diethyl ether; water; acetone | 49% |
With sodium methylate; piperdinium acetate; acetic acid In diethyl ether; water; acetone | 49% |
Conditions | Yield |
---|---|
In water for 2h; Heating; Yield given; |
2-amino-6-methyl-4-oxo-4H-pyran-3-carbonitrile
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / HCl / H2O / 4 h / Heating 2: 75 percent / POCl3; PCl5 / CHCl3 / 6 h / Heating 3: 88 percent / H2 / Pd-C / methanol / 20 °C View Scheme |
4-hydroxy-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / POCl3; PCl5 / CHCl3 / 6 h / Heating 2: 88 percent / H2 / Pd-C / methanol / 20 °C View Scheme |
5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / KOH / aq. ethanol / 4 h / Heating 2: 57 percent / copper powder / quinoline / 3 h / Heating View Scheme |
piperidine
potassium carbonate
cyanoacetic acid amide
formic acid ethyl ester
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With sodium methylate In water; acetic acid; acetone |
trans-4-methoxy-3-buten-2-one
cyanoacetic acid amide
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
In 2-methoxy-ethanol; water; acetic acid |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
2-chloro-6-methylnicotinonitrile
Conditions | Yield |
---|---|
With trichlorophosphate at 130℃; for 2h; Inert atmosphere; | 99% |
With trichlorophosphate at 80 - 90℃; for 2.5h; | 94% |
With trichlorophosphate In 1,4-dioxane at 80℃; for 1h; | 77% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
thiourea
Conditions | Yield |
---|---|
With iodine In water for 1h; | 96% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
Stage #1: 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile With ammonium hydroxide; nickel In methanol at 50℃; Inert atmosphere; Stage #2: With hydrogenchloride In ethyl acetate for 0.5h; Cooling with ice; | 93.5% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
5-bromo-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With N-Bromosuccinimide In 1,2-dichloro-ethane Heating; | 92% |
With N-Bromosuccinimide In 1,2-dichloro-ethane for 18h; Reflux; | 92.3% |
With N-Bromosuccinimide In 1,2-dichloro-ethane at 85℃; for 7h; | 91% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
6-Methylpyrid-2-one-3-carboxylic Acid
Conditions | Yield |
---|---|
With sodium hydroxide at 140℃; for 24h; pressure vessel; | 85% |
In sodium hydroxide | 81% |
In sodium hydroxide | 81% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile With 1,1,1,3,3,3-hexamethyl-disilazane In toluene at 120℃; for 2h; Inert atmosphere; Stage #2: With diisobutylaluminium hydride In toluene at 0℃; for 9h; Inert atmosphere; | 85% |
Stage #1: 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile With 1,1,1,3,3,3-hexamethyl-disilazane In toluene for 2h; Inert atmosphere; Heating; Stage #2: With diisobutylaluminium hydride In toluene at 0℃; Inert atmosphere; | 82% |
With hydrogenchloride; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane 1) toluen, refl. 3 hrs., 2) -42 deg C, 6 hrs.; Yield given. Multistep reaction; |
trimethoxonium tetrafluoroborate
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
2-methoxy-6-methylpyridine-3-carbonitrile
Conditions | Yield |
---|---|
In dichloromethane for 48h; Ambient temperature; | 83% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
1,2-dihydro-6-<(hydroxyimino)methyl>-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With n-Butyl nitrite; ammonia; potassium amide In diethyl ether for 1h; | 80% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
4-bromobutanenitrile
2-(3-cyanopropoxy)-6-methylpyridine-3-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80 - 90℃; for 2h; | 76% |
benzyl chloride
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
2-(benzyloxy)-6-methylnicotinonitrile
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; zinc(II) oxide; zinc(II) chloride In 1,4-dioxane at 110℃; Inert atmosphere; | 73% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
2-bromo-6-methylpyridine-3-carbonitrile
Conditions | Yield |
---|---|
With phosphorus pentaoxide; sodium bicarbonate; sodium chloride; tetrabutylammomium bromide In water; toluene | 72.5% |
With phosphorus pentoxide; tetrabutylammomium bromide In toluene for 5h; Reflux; |
2-Methyl-1-phenyl-2-propanol
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
C17H18N2O
Conditions | Yield |
---|---|
With sulfuric acid In benzene at 60 - 70℃; for 0.5h; | 72% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
phenylmagnesium bromide
3-Benzoyl-6-methyl-2-oxopyridine
Conditions | Yield |
---|---|
In diethyl ether for 4h; Heating; | 68% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
cyclopentylmagnesium bromide
Conditions | Yield |
---|---|
In diethyl ether for 4h; Heating; | 63% |
1-bromo-butane
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
6-Butyl-3-cyano-2-pyridone
Conditions | Yield |
---|---|
Stage #1: 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -50 - 43℃; for 2.25h; Stage #2: 1-bromo-butane In tetrahydrofuran; hexanes at -50 - 25℃; for 1h; | 61% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-cyano-6-methylpyridin-2-one
Conditions | Yield |
---|---|
With potassium hydroxide In water; acetone at 20℃; Condensation; | 57% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
allyl bromide
1-allyl-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 0 - 65℃; | 57% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | A 31% B 56% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
methyl iodide
A
3-cyano-6-ethyl-2(1H)-pyridinone
B
6-isopropyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
Stage #1: 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 18h; | A 50% B 18% |
methyl magnesium iodide
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
3-acetyl-6-methyl-2-(1H)pyridone
Conditions | Yield |
---|---|
In diethyl ether for 4h; Heating; | 46% |
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
6-methyl-5-nitro-2-oxo-1,2-dihydropyridine-3-carbonitrile
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid for 4h; Cooling with ice; | 45% |
di-tert-butyl dicarbonate
1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel dichloride In methanol at 0 - 20℃; for 15h; | 35% |
IUPAC Name: 6-methyl-2-oxo-1H-pyridine-3-carbonitrile
Empirical Formula: C7H6N2O
Molecular Weight: 134.1353g/mol
EINECS: 224-202-5
Structure of 3-Pyridinecarbonitrile,1,2-dihydro-6-methyl-2-oxo- (CAS NO.4241-27-4):
Melting Point: 293-295 °C
Water Solubility: 2.38 g/L (20 ºC)
Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Heterocycles;Pyridine
Chemical Properties: SLIGHTLY YELLOW GRANULAR CRYSTALLINE POWDER
Canonical SMILES: CC1=CC=C(C(=O)N1)C#N
InChI: InChI=1S/C7H6N2O/c1-5-2-3-6(4-8)7(10)9-5/h2-3H,1H3,(H,9,10)
InChIKey: FIMGYEKEYXUTGD-UHFFFAOYSA-N
Hazard Codes: Xn,Xi
Risk Statements: 36/37/38-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-26-22-36
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S22:Do not breathe dust.
S36:Wear suitable protective clothing.
RIDADR: 3276
PackingGroup: III
3-Pyridinecarbonitrile,1,2-dihydro-6-methyl-2-oxo- , its cas register number is 4241-27-4. It also can be called NSC 15124 ; 1,2-Dihydro-6-methyl-2-oxonicotinonitrile ; Nicotinonitrile, 1,2-dihydro-6-methyl-2-oxo- (8CI) . 3-Pyridinecarbonitrile,1,2-dihydro-6-methyl-2-oxo- (CAS NO.4241-27-4) is irritating to eyes, respiratory system and skin. And it's also harmful by inhalation, in contact with skin and if swallowed. So you should wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
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