-
Name
Methyl 2-aminonicotinate
- EINECS 681-092-5
- CAS No. 14667-47-1
- Article Data31
- CAS DataBase
- Density 1.238 g/cm3
- Solubility
- Melting Point 84-86 °C
- Formula C7H8N2O2
- Boiling Point 251.3 °C at 760 mmHg
- Molecular Weight 152.153
- Flash Point 105.8 °C
- Transport Information
- Appearance
- Safety 22-26-36/37/39
- Risk Codes 20/21/22-36/37/38
-
Molecular Structure
-
Hazard Symbols
Xn
- Synonyms Nicotinicacid, 2-amino-, methyl ester (7CI,8CI);2-Amino-3-methoxycarbonylpyridine;2-Amino-3-pyridinecarboxylic acid methyl ester;2-Aminonicotinic acid methylester;Methyl 2-amino-3-pyridinecarboxylate;NSC522516;
- PSA 65.21000
- LogP 1.03160
Synthetic route
-
-
5345-47-1
2-aminopyridin-3-carboxylic acid
-
-
18107-18-1
diazomethyl-trimethyl-silane
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| In methanol; toluene at 0℃; for 0.5h; | 95% |
| In methanol; diethyl ether; toluene at 0℃; for 0.75h; Inert atmosphere; | 90% |
| In methanol; hexane for 0.5h; |
-
-
5345-47-1
2-aminopyridin-3-carboxylic acid
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| With triethylamine In methanol at 20℃; for 1h; | 94% |
| Conditions | Yield |
|---|---|
| With sulfuric acid at 0 - 60℃; under 760.051 Torr; for 1.5h; Inert atmosphere; Microwave irradiation; | 93% |
| With thionyl chloride at 0 - 80℃; for 3h; | 86% |
| With sulfuric acid at 80℃; for 7h; | 63% |
-
-
5345-47-1
2-aminopyridin-3-carboxylic acid
-
-
37091-73-9
2-chloro-1,3-dimethylimidazolinium chloride
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| With triethylamine In methanol for 1h; Ambient temperature; | 84% |
-
-
5345-47-1
2-aminopyridin-3-carboxylic acid
-
-
74-88-4
methyl iodide
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-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| With potassium carbonate In dimethyl sulfoxide at 20℃; for 18h; Reflux; | 71% |
| With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Reflux; | 58% |
| Stage #1: 2-aminopyridin-3-carboxylic acid With potassium carbonate In N,N-dimethyl-formamide Reflux; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 18h; Reflux; | 58% |
| With potassium carbonate In N,N-dimethyl-formamide for 18h; | 3.2 g |
-
-
186581-53-3, 908094-01-9
diazomethane
-
-
5345-47-1
2-aminopyridin-3-carboxylic acid
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| In methanol; diethyl ether at 0℃; |
-
-
1462-86-8
3-amino-pyridine-2-carboxylic acid
-
-
18107-18-1
diazomethyl-trimethyl-silane
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| With methanol In diethyl ether; toluene at 20℃; Inert atmosphere; |
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| With dodecacarbonyl-triangulo-triruthenium; 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane; isopropyl alcohol at 140℃; for 24h; Inert atmosphere; Sealed tube; | 70 %Spectr. |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
433226-06-3
2-amino-5-bromonicotinic acid ethyl ester
| Conditions | Yield |
|---|---|
| With bromine; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 1h; | 99% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
50735-34-7
methyl 2-amino-5-bromopyridine-3-carboxylate
| Conditions | Yield |
|---|---|
| With bromine; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 1h; | 99% |
| With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 2h; | 77% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
603-35-0
triphenylphosphine
-
-
199733-96-5
N-(3-methoxycarbonyl-2-pyridyl)triphenyliminophosphorane
| Conditions | Yield |
|---|---|
| With hexachloroethane; triethylamine In benzene for 3.5h; Heating; | 98% |
| With diethylazodicarboxylate In dichloromethane; toluene at 20℃; for 2.16667h; Mitsunobu type reaction; | 87% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
5327-31-1
2-aminonicotinic acid hydrazide
| Conditions | Yield |
|---|---|
| With hydrazine hydrate In ethanol at 90℃; for 15h; Inert atmosphere; | 96% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
21038-22-2
O-(4-methoxybenzyl)hydroxylamine
-
-
1268706-67-7
C14H15N3O3
| Conditions | Yield |
|---|---|
| With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 2h; | 95% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
50735-33-6
methyl 2-amino-5-chloro-3-pyridinecarboxylate
| Conditions | Yield |
|---|---|
| With N-chloro-succinimide In acetonitrile at 60℃; for 6h; Concentration; Temperature; Solvent; | 93% |
| With hydrogenchloride; tert-butylhypochlorite In methanol | 26% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
1391062-92-2
2-aminonicotinic acid methyl ester N-oxide
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃; | 88% |
| With dihydrogen peroxide In ethanol; water at 20℃; for 3h; | 78% |
| Stage #1: methyl 2-aminonicotinate With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol at 20℃; for 3h; Stage #2: manganese(IV) oxide In ethanol | 63% |
| With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃; for 3h; | 63% |
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-
75-44-5
phosgene
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-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| Stage #1: phosgene; 6-amino-7-fluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one In 1,4-dioxane at 0℃; for 10.5h; Reflux; Stage #2: methyl 2-aminonicotinate In 1,4-dioxane for 6h; Inert atmosphere; Reflux; | 87% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
75-16-1
methylmagnesium bromide
-
-
213666-96-7
2-(2-aminopyridin-3-yl)propan-2-ol
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -20 - 20℃; for 2.5h; Inert atmosphere; | 86% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
598-31-2
1-bromoacetone
-
-
133427-09-5
methyl 2-methyl-imidazo[1,2-α]pyridine-8-carboxylate
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In ethanol | 85% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
42926-52-3
2-ethoxybenzoyl chloride
| Conditions | Yield |
|---|---|
| With triethylamine In dichloromethane at 0 - 20℃; for 4h; | 85% |
| With triethylamine In dichloromethane at 0 - 20℃; |
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-
75-44-5
phosgene
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-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| Stage #1: phosgene; 6-amino-2,2,7-trifluoro-4-(4-methoxybenzyl)-2H-benzo[b][1,4]oxazine-3(4H)-one In 1,4-dioxane at 0℃; for 10.5h; Reflux; Stage #2: methyl 2-aminonicotinate In 1,4-dioxane for 6h; Inert atmosphere; Reflux; | 85% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
98-59-9
p-toluenesulfonyl chloride
| Conditions | Yield |
|---|---|
| With pyridine at 20℃; for 24h; | 84% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
88312-64-5
2-amino-3-(methoxycarbonyl)-5-nitropyridine
| Conditions | Yield |
|---|---|
| With sulfuric acid; nitric acid at 0 - 20℃; for 2h; Inert atmosphere; regioselective reaction; | 82% |
| With sulfuric acid; nitric acid at 0 - 70℃; for 23.75h; | 68% |
| Stage #1: methyl 2-aminonicotinate With sulfuric acid; nitric acid; sodium hydrogencarbonate at 0 - 70℃; for 23.66h; Stage #2: With sodium hydrogencarbonate In water at 0℃; | 35% |
| Stage #1: methyl 2-aminonicotinate With sulfuric acid; nitric acid at 0 - 70℃; for 23.6667h; Stage #2: With sodium hydrogencarbonate In water at 0℃; | 35% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
1711-05-3
m-anisoyl chloride
| Conditions | Yield |
|---|---|
| With triethylamine at 0 - 20℃; for 12h; | 79% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
123-66-0
Ethyl hexanoate
-
-
115891-79-7
3-Butyl-4-hydroxy-1H-[1,8]naphthyridin-2-one
| Conditions | Yield |
|---|---|
| With potassium tert-butylate 1.) 0.25 h, 2.) heating, 4 h; | 76% |
-
-
14667-47-1
methyl 2-aminonicotinate
-
-
24424-99-5
di-tert-butyl dicarbonate
-
-
877593-10-7
methyl 2-[bis(tert-butoxycarbonyl)amino]nicotinate
| Conditions | Yield |
|---|---|
| With dmap In dichloromethane at 20℃; for 36h; | 75% |
| With dmap In dichloromethane for 48h; Inert atmosphere; |
| Conditions | Yield |
|---|---|
| With copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 48h; Inert atmosphere; | 73.2% |
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-
14667-47-1
methyl 2-aminonicotinate
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-
463-71-8
thiophosgene
-
-
1360964-43-7
methyl 2-isothiocyanatonicotinate
| Conditions | Yield |
|---|---|
| In dichloromethane at 0℃; for 2h; | 70.51% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
98-88-4
benzoyl chloride
-
-
144267-78-7
methyl 2-(N-benzoylamino)-nicotinate
| Conditions | Yield |
|---|---|
| With triethylamine at 0 - 20℃; for 12h; | 69% |
| With pyridine Yield given; |
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10400-19-8
3-pyridinecarbonyl chloride
-
-
14667-47-1
methyl 2-aminonicotinate
| Conditions | Yield |
|---|---|
| With triethylamine at 0 - 20℃; for 12h; | 68% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
2555-49-9
phenoxyacetic acid ethyl ester
-
-
1367847-18-4
C14H10N2O3
| Conditions | Yield |
|---|---|
| With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; | 67% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
108-24-7
acetic anhydride
-
-
3809-93-6
2-Methyl-4H-pyrido<2,3-d><3,1>oxazin-4-one
| Conditions | Yield |
|---|---|
| at 20℃; | 65% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
84379-72-6
1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate
| Conditions | Yield |
|---|---|
| With diphenyl hydrogen phosphate In 1,4-dioxane at 20℃; for 15h; Minisci Aromatic Substitution; Sealed tube; Irradiation; Glovebox; Inert atmosphere; Green chemistry; | 65% |
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-
14667-47-1
methyl 2-aminonicotinate
-
-
25068-94-4
(2-iodo-phenyl)-methanesulfonyl chloride
-
-
1362699-05-5
methyl 2-{[(2-iodobenzyl)sulfonyl]amino}nicotinate
| Conditions | Yield |
|---|---|
| Stage #1: methyl 2-aminonicotinate; (2-iodo-phenyl)-methanesulfonyl chloride With pyridine In dichloromethane at 20℃; for 12h; Stage #2: With hydrogenchloride In dichloromethane; water | 63% |
Methyl 2-aminonicotinate Specification
The 3-Pyridinecarboxylicacid, 2-amino-, methyl ester, with the CAS registry number 14667-47-1, has the systematic name and IUPAC name of methyl 2-aminopyridine-3-carboxylate. And the molecular formula of this chemical is C7H8N2O2. It belongs to the following product categories: Pharmacetical; Pyridine series; API intermediates; Pyridine.
The physical properties of 3-Pyridinecarboxylicacid, 2-amino-, methyl ester are as following: (1)ACD/LogP: 1.90; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 1.9; (5)ACD/BCF (pH 5.5): 14.05; (6)ACD/BCF (pH 7.4): 16.26; (7)ACD/KOC (pH 5.5): 221.18; (8)ACD/KOC (pH 7.4): 256.07; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 42.43 Å2; (13)Index of Refraction: 1.57; (14)Molar Refractivity: 40.35 cm3; (15)Molar Volume: 122.8 cm3; (16)Polarizability: 15.99×10-24cm3; (17)Surface Tension: 53.4 dyne/cm; (18)Density: 1.238 g/cm3; (19)Flash Point: 105.8 °C; (20)Enthalpy of Vaporization: 48.86 kJ/mol; (21)Boiling Point: 251.3 °C at 760 mmHg; (22)Vapour Pressure: 0.0206 mmHg at 25°C.
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin, it is also harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Do not breathe dust; Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1cccnc1N
(2)InChI: InChI=1/C7H8N2O2/c1-11-7(10)5-3-2-4-9-6(5)8/h2-4H,1H3,(H2,8,9)
(3)InChIKey: NZZDEODTCXHCRS-UHFFFAOYAY
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