Conditions | Yield |
---|---|
With potassium hydroxide; bromine 1.) RT, 1 h, 2.) 70 deg C, 15 min; | 67% |
With sodium hydroxide; bromine In tetrahydrofuran at 5 - 70℃; Hoffmann rearrangement; |
2-amino-3-methyl-5-nitropyridine
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With hydrazine In water at 110 - 120℃; for 5h; | 45% |
Multi-step reaction with 3 steps 1: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser 2: phosphoryl chloride 3: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation View Scheme | |
Multi-step reaction with 2 steps 1: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser 2: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation View Scheme |
Conditions | Yield |
---|---|
With hydrazine In water at 110 - 120℃; for 5h; | 41% |
2-chloro-3-methyl-5-nitropyridine
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With palladium on activated charcoal; sodium acetate; acetic acid Hydrogenation; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight 2: thionyl chloride / Heating 3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / Heating 2: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 3: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min View Scheme |
5-methyl-nicotinic acid chloride
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 2: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2SO4; HNO3 2: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser 3: phosphoryl chloride 4: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation View Scheme | |
Multi-step reaction with 3 steps 1: H2SO4; HNO3 2: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser 3: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation View Scheme |
2-hydroxy-3-methyl-5-nitropyridine
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: phosphoryl chloride 2: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation View Scheme |
2-bromo-3-methyl-5-nitropyridine
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); ammonia; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine; sodium t-butanolate In 1,4-dioxane for 24h; Reagent/catalyst; | 86 %Chromat. |
3-chloro-5-nitropyridine
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In methanol |
5-methylpyridin-3-amine
di-tert-butyl dicarbonate
tert-butyl N-(5-methylpyridin-3-yl)carbamate
Conditions | Yield |
---|---|
Stage #1: 5-methylpyridin-3-amine With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; | 88% |
With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; | 88% |
Stage #1: 5-methylpyridin-3-amine With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h; Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; | 88% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; | 86% |
Conditions | Yield |
---|---|
Stage #1: N-Benzyloxycarbonyl-L-proline With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 0 - 70℃; for 25h; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 79% |
5-methylpyridin-3-amine
1,1'-carbonyldiimidazole
1,3-bis(5-methylpyridin-3-yl)urea
Conditions | Yield |
---|---|
In toluene at 20 - 80℃; | 75% |
Conditions | Yield |
---|---|
With sodium hydroxide In toluene at 100℃; for 10h; | 75% |
In toluene at 100℃; for 10h; | 75% |
5-methylpyridin-3-amine
phenyl chloroformate
(5-methyl-pyridin-3-yl)-carbamic acid phenyl ester
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran | 71% |
With pyridine In tetrahydrofuran at 0℃; | 71% |
Conditions | Yield |
---|---|
With N,N,N'N'-tetramethyl-1,3-propanediamine; boric acid In 1,3,5-trimethyl-benzene at 164℃; for 7h; Dean-Stark; Inert atmosphere; Green chemistry; regiospecific reaction; | 70% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With acetic acid at 120℃; for 12h; | 64.5% |
In acetic acid for 18h; Reflux; |
5-methylpyridin-3-amine
3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoic acid
3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamide
Conditions | Yield |
---|---|
With 4-pyrrolidin-1-ylpyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 17h; | 61% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; carbonic acid dimethyl ester In tetrahydrofuran; dichloromethane at 20℃; | 53.9% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
Stage #1: 4-(((4-(tert-butyl)phenyl)sulfonamido)methyl)benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 20 - 66℃; for 3h; Stage #2: 5-methylpyridin-3-amine With pyridine at 20℃; for 16h; | 50% |
5-methylpyridin-3-amine
2,4-dibromo-butyryl bromide
Conditions | Yield |
---|---|
Stage #1: 5-methylpyridin-3-amine; 2,4-dibromo-butyryl bromide In dichloromethane at 0 - 20℃; for 3h; Stage #2: With sodium hydroxide In dichloromethane; water at 20℃; for 3h; | 49.2% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane; toluene at 20℃; for 0.5h; | 46.3% |
5-methylpyridin-3-amine
bis(trichloromethyl) carbonate
Conditions | Yield |
---|---|
Stage #1: 5-methylpyridin-3-amine; bis(trichloromethyl) carbonate; (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine In tetrahydrofuran at 30℃; for 1h; Stage #2: 5-methylpyridin-3-amine With triethylamine at 30 - 65℃; for 16h; | 45% |
Stage #1: bis(trichloromethyl) carbonate; (4S)-7-(2-methylpyridin-4-yl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine In tetrahydrofuran at 30℃; for 1h; Stage #2: 5-methylpyridin-3-amine With triethylamine In tetrahydrofuran at 65℃; for 16h; | 45% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
Stage #1: 5-methylpyridin-3-amine With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 1-(5-(4,6-dichloropyrimidin-2-yl)-2-methylpiperidin-1-yl)ethan-1-one In tetrahydrofuran at 20℃; for 16h; | 45% |
5-methylpyridin-3-amine
bis(trichloromethyl) carbonate
(S)-N-[1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine
N-(3-{(1S)-1-[(6-chloropyrazin-2-yl)amino]ethyl}phenyl)-N'-(5-methylpyridin-3-yl)urea
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; (S)-N-[1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine With sodium hydrogencarbonate In dichloromethane; water for 3h; Stage #2: 5-methylpyridin-3-amine In dichloromethane; water for 17h; | 42% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With pyridine; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; | 39.6% |
5-methylpyridin-3-amine
iodobenzene
bis(pinacol)diborane
3-methyl-5-phenylpyridine
Conditions | Yield |
---|---|
Stage #1: 5-methylpyridin-3-amine; bis(pinacol)diborane With tert.-butylnitrite In acetonitrile at 80℃; for 2h; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; | 35% |
5-methylpyridin-3-amine
2-methoxycarbonylbenzenesulfonyl chloride
methyl 2-{[(5-methylpyridin-3-yl)amino]sulfonyl}benzoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; | 34% |
5-methylpyridin-3-amine
bis(trichloromethyl) carbonate
(S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-N-(5-methylpyridin-3-yl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; (S)-6-(3-(3-fluoropyrrolidin-1-yl)phenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 60℃; for 18h; | 31% |
5-methylpyridin-3-amine
bis(trichloromethyl) carbonate
7-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-1,8-naphthyridine
N-(5-methylpyridin-3-yl)-7-(3-(trifluoromethyl)phenyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; 7-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-1,8-naphthyridine With triethylamine In tetrahydrofuran at 30℃; for 0.5h; Inert atmosphere; Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 60℃; for 18h; Inert atmosphere; | 27% |
5-methylpyridin-3-amine
A
3-amino-2,6-dibromo-5-methylpyridine
B
3-amino-2-bromo-5-methylpyridine
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide at 70℃; for 1h; Product distribution; | A 26% B 6% C 0.5% |
With hydrogen bromide; dihydrogen peroxide at 70℃; for 1h; | A 26% B 6% C 0.5% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; caesium carbonate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; | 22% |
5-methylpyridin-3-amine
bis(trichloromethyl) carbonate
2,2-dimethyl-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine
2,2-dimethyl-N-(5-methylpyridin-3-yl)-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-2H-pyrido[3,2-b][1,4]oxazine-4(3H)-carboxamide
Conditions | Yield |
---|---|
Stage #1: bis(trichloromethyl) carbonate; 2,2-dimethyl-6-(3-(pyrrolidin-1-ylmethyl)phenyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine With triethylamine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 5-methylpyridin-3-amine In tetrahydrofuran at 60℃; | 20% |
5-methylpyridin-3-amine
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 20℃; | 20% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water at 0℃; for 2h; | 19% |
Molecule structure of 3-Amino-5-Methylpyridine (CAS NO.3430-19-1) :
IUPAC Name: (2S)-2-amino-3-(3-chloro-4-hydroxyphenyl)propanoic acid
Molecular Weight: 215.6336 g/mol
Molecular Formula: C9H10ClNO3
Density: 1.068 g/cm3
Melting Point: 59-63 °C
Boiling Point: 261.1 °C at 760 mmHg
Flash Point: 135.6 °C
Molar Volume: 101.2 cm3
Polarizability: 13.24*10-24 cm3
Surface Tension: 46.9 dyne/cm
Enthalpy of Vaporization: 49.88 kJ/mol
Vapour Pressure: 0.0118 mmHg at 25 °C
XLogP3: -1.8
H-Bond Donor: 3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Tautomer Count: 3
Exact Mass: 215.034921
MonoIsotopic Mass: 215.034921
Topological Polar Surface Area: 83.6
Heavy Atom Count: 14
Complexity: 212
Defined Atom StereoCenter Count: 1
Canonical SMILES: C1=CC(=C(C=C1CC(C(=O)O)N)Cl)O
Isomeric SMILES: C1=CC(=C(C=C1C[C@@H](C(=O)O)N)Cl)O
InChI: InChI=1S/C9H10ClNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
InChIKey: ACWBBAGYTKWBCD-ZETCQYMHSA-N
Product Categories of 3-Amino-5-Methylpyridine (CAS NO.3430-19-1) : VARIOUSAMINE; Heterocyclic Compounds; Amino; Intermediate; Pyridine; Boronic Acid; Heterocyclic Building Blocks; Pyridines; Building Blocks
Hazard Codes: T, Xi, Xn
Risk Statements: 22-37/38-41-20/21/22
R22: Harmful if swallowed
R37/38: Irritating to respiratory system and skin
R41:Risk of serious damage to the eyes
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-36/37/39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S36: Wear suitable protective clothing
Hazard Note: Toxic
3-Amino-5-Methylpyridine (CAS NO.3430-19-1) is also called 3-Amino-5-picoline ; 5-Methyl-pyridin-3-ylamine ; 3-Amino-5-methylpyridine97% ; 3-Pyridinamine,5-methyl-(9CI) ; 5-Methyl-3-pyridylamine hydrochloride salt ; 5-Methyl-3-pyridinamine ; 5-Amino-3-methylpyridine .
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