5470-70-2

Basic information

• Product Name: Methyl 6-methylnicotinate
• Synonyms: LABOTEST-BB LT00847843;METHYL 6-METHYLPYRIDINE-3-CARBOXYLATE;METHYL 6-METHYLNICOTINATE;3-PYRIDINECARBOXYLIC ACID, 6-METHYL-, METHYL ESTER;6-METHYL PYRIDINE-3-CARBOXYLIC ACID METHYL ESTER;6-METHYLNICOTINIC ACID METHYL ESTER;5-CARBOMETHOXY-2-PICOLINE;Methyl-6-methylnictinate
• CAS NO: 5470-70-2
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 1308068-626-2
• Product Categories: CARBOXYLICESTER;Acids and Derivatives;Heterocycles;Esters;Pyridines;Organic acids;Nicotine Derivatives;Pyridine;Aromatics
• Mol File: 5470-70-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 34-37 °C(lit.)
• Boiling Point: 160 °C106 mm Hg(lit.)
• Flash Point: 218 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.2023 (rough estimate)
• Vapor Pressure: 0.0736mmHg at 25°C
• Refractive Index: 1.5810 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 3.92±0.10(Predicted)
• BRN: 122940
• CAS DataBase Reference: Methyl 6-methylnicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 6-methylnicotinate(5470-70-2)
• EPA Substance Registry System: Methyl 6-methylnicotinate(5470-70-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 5470-70-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 5470-70-2 differently. You can refer to the following data:
1. It is used in the treatment of CNS disorders using D-amino acid oxidase and D-aspartate oxidase inhibitors.
2. Methyl 6-methylnicotinate is used in the treatment of CNS disorders using D-amino acid oxidase and D-aspartate oxidase inhibitors.
3. Methyl 6-methylpyridine-3-carboxylate may be used in chemical synthesis studies.

Chemical Properties

Brown Solid

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 4409, 1975 DOI: 10.1021/ja00848a053

InChI:InChI=1/C8H9NO2/c1-6-3-4-7(5-9-6)8(10)11-2/h3-5H,1-2H3

Synthetic route

5-(methoxycarbonyl)-2-methylpyridine 1-oxide (49668-89-5) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With indium; cobalt(II) chloride In methanol at 20℃; for 2h; sonication;	80%

methanol (67-56-1) + 6-methylnicotinic acid (3222-47-7) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With sulfuric acid for 17h; Reflux;	75%
With sulfuric acid for 21h; Heating; Yield given;
With sulfuryl dichloride

propynoic acid methyl ester (922-67-8) + C-ethoxy-N-isopropenylmethanimine → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
In benzene for 5h; Heating;	41%

1,3-DIOXOLANE (646-06-0) + methyl 3-pyridinecarboxylate (93-60-7) → Methyl 6-methylnicotinate (5470-70-2) + Methyl 4,6-Dimethylnicotinate (69971-44-4)

Conditions	Yield
With sulfuric acid for 7h; Irradiation;	A 21% B 5%

(+/-)-(E)-methyl 3-(but-3-yn-2-yloxy)acrylate (1211000-51-9) + N-methoxylamine hydrochloride (593-56-6) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With sodium acetate In ethanol at 150℃; for 3h; Inert atmosphere; Microwave irradiation;	14%

methanol (67-56-1) + methyl 3-pyridinecarboxylate (93-60-7) → 4-methylnicotinic acid methyl ester (33402-75-4) + Methyl 6-methylnicotinate (5470-70-2) + 2-methoxynicotinic acid methyl ester (67367-26-4) + 6-methoxy-nicotinic acid methyl ester (26218-80-4)

Conditions	Yield
With sulfuric acid for 1h; Product distribution; Mechanism; Irradiation; effect of additives; variation of temp., acid concn.; further alcohol;	A 7.1% B 9.5% C 8.8% D 3.8%
With sulfuric acid for 1h; Irradiation;	A 7.1% B 9.5% C 8.8% D 3.8%
With sulfuric acid at 32℃; for 0.833333h; Product distribution; Mechanism; Irradiation; var. reagent, acid concentration and time;

methanol (67-56-1) + 6-methyl-nicotinoyl chloride (51598-76-6) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
In dichloromethane Ambient temperature;
With triethylamine for 3h;

methyl 3-pyridinecarboxylate (93-60-7) + methylmagnesium chloride (676-58-4) + phenyl chloroformate (1885-14-9) → 4-methylnicotinic acid methyl ester (33402-75-4) + Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With sulfur Yield given. Multistep reaction;
With sulfur Yield given. Multistep reaction;

6-methyl-nicotinic acid-hydrochloride → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With hydrogenchloride

6-methylnicotinic acid (3222-47-7) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 2 h / Heating 2: CH2Cl2 / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / 3 h View Scheme

6-methylnicotinic acid (3222-47-7) + sodium hydrogencarbonate (144-55-8) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
In methanol

methanol (67-56-1) + 6-methyl-3-pyridinemethanol (34107-46-5) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 24h; Schlenk technique; Green chemistry;	92%Chromat.

5-ethyl-2-methyl-pyridine (104-90-5) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
With sulfuric acid; nitric acid at 150℃;

5-Hydroxy-2-methylpyridine (1121-78-4) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: fluorosulfonyl fluoride; triethylamine / dichloromethane / 24 h / 20 °C / 760.05 Torr 2: bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline; manganese / N,N-dimethyl-formamide / 20 h / 20 °C / 760.05 Torr / Schlenk technique; Inert atmosphere; Glovebox 3: methanol View Scheme

diazomethane (186581-53-3, 908094-01-9) + 6-methylnicotinic acid (3222-47-7) → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
In methanol	54.2 mg

6-methylpyridin-3-yl sulfurofluoridate → Methyl 6-methylnicotinate (5470-70-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline; manganese / N,N-dimethyl-formamide / 20 h / 20 °C / 760.05 Torr / Schlenk technique; Inert atmosphere; Glovebox 2: methanol View Scheme

Methyl 6-methylnicotinate (5470-70-2) → 6-methyl-3-pyridinemethanol (34107-46-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at -5 - 23℃; for 2h;	100%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3h;	98%
Stage #1: Methyl 6-methylnicotinate With lithium aluminium tetrahydride In diethyl ether at 55℃; for 1.5h; Heating / reflux; Stage #2: With water In diethyl ether at 0℃; for 1h;	97%

Methyl 6-methylnicotinate (5470-70-2) → 5-(methoxycarbonyl)-2-methylpyridine 1-oxide (49668-89-5)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; Inert atmosphere;	100%
With dihydrogen peroxide; sodium tungstate In water at 60 - 80℃; for 5.66667h;	98%
Stage #1: Methyl 6-methylnicotinate With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 24℃; for 6h; Stage #2: manganese(IV) oxide In dichloromethane; water	91%

Methyl 6-methylnicotinate (5470-70-2) → methyl 6-methylpiperidine-3-carboxylate.hydrochloride (1009376-74-2)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; water at 80℃; under 3102.97 Torr; for 21h;	100%
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol at 75℃; under 2844.39 Torr;	100%

Methyl 6-methylnicotinate (5470-70-2) → 6-methylnicotinic acid (3222-47-7)

Conditions	Yield
	100%

Methyl 6-methylnicotinate (5470-70-2) → 6-methyl-3-piperidinecarboxylic acid methyl ester (908245-03-4)

Conditions	Yield
With hydrogenchloride; hydrogen; 1% Pd/C In methanol; water at 80℃; under 3102.97 Torr; for 21h; Inert atmosphere;	100%
With hydrogenchloride; platinum(IV) oxide; hydrogen In methanol; water at 50℃; under 2585.81 Torr; for 15h;	96.15%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In methanol; water under 2534.09 Torr; for 24h;

Methyl 6-methylnicotinate (5470-70-2) + acetic acid (64-19-7) → methyl 6-methylpiperidine-3-carboxylate acetic acid

Conditions	Yield
With platinum(IV) oxide; hydrogen at 60℃; under 7500.75 Torr; Autoclave;	100%

Methyl 6-methylnicotinate (5470-70-2) → 6-methylpyridine-3-carbohydrazide (197079-25-7)

Conditions	Yield
With hydrazine In methanol at 20℃; for 2h;	98%
With hydrazine hydrate In ethanol for 2h; Reflux;	90%
With hydrazine hydrate In ethanol at 20℃; for 2h;	90%

Methyl 6-methylnicotinate (5470-70-2) + sodium tungstate (VI) dihydrate (10213-10-2) → 5-(methoxycarbonyl)-2-methylpyridine 1-oxide (49668-89-5)

Conditions	Yield
With dihydrogen peroxide In methanol; water	98%

Methyl 6-methylnicotinate (5470-70-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C14H22BNO4

Conditions	Yield
With 1,3-di-tert-butyl-2-(neopentyloxy)-2,3-dihydro-1H-1,3,2-diazaphosphole In diethyl ether at 20℃; for 12h;	96%

Methyl 6-methylnicotinate (5470-70-2) + N,0-dimethylhydroxylamine (1117-97-1) → N-methoxy-N-methyl-6-methylnicotinamide (221615-71-0)

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran at -10 - 5℃; for 2.5h;	94.3%
With isopropylmagnesium chloride In tetrahydrofuran; toluene at -10℃; for 0.5h;

Methyl 6-methylnicotinate (5470-70-2) + 1-bromoacetone (598-31-2) → methyl 2-methyl-indolizine-6-carboxylate (207791-84-2)

Conditions	Yield
Stage #1: Methyl 6-methylnicotinate; 1-bromoacetone In acetone Heating; Stage #2: With sodium carbonate In ethanol for 3h; Heating;	93%

Methyl 6-methylnicotinate (5470-70-2) → 6-methylnicotinamide (6960-22-1)

Conditions	Yield
With ammonia In ethanol at 80℃; for 72h;	91%
With ammonia; water at 20℃; for 4h;	72%

Methyl 6-methylnicotinate (5470-70-2) + lithium 4-(methylthio)phenylacetate → 1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone (221615-72-1)

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h; Reagent/catalyst; Temperature;	87.7%

Methyl 6-methylnicotinate (5470-70-2) + trifluoromethylsulfonic anhydride (358-23-6) + triphenylphosphine (603-35-0) → (5-(methoxycarbonyl)-2-methylpyridin-4-yl)triphenylphosphonium trifluoromethanesulfonate

Conditions	Yield
Stage #1: Methyl 6-methylnicotinate; trifluoromethylsulfonic anhydride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: triphenylphosphine With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -78 - 20℃;	83%
at -78 - 20℃; Alkaline conditions;	83%

methanol (67-56-1) + Methyl 6-methylnicotinate (5470-70-2) → Methyl 4,6-Dimethylnicotinate (69971-44-4)

Conditions	Yield
With Ethyl 2-mercaptopropionate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; toluene-4-sulfonic acid In dimethyl sulfoxide at 23℃; UV-irradiation;	82%

Methyl 6-methylnicotinate (5470-70-2) + isoxazolidine hydrochloride (39657-45-9) → isoxazolidine-2-yl-(6-methylpyridin-3-yl)methanone

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran; toluene at -20 - -10℃; for 0.5h; Reagent/catalyst; Inert atmosphere;	80%

Methyl 6-methylnicotinate (5470-70-2) + propiononitrile (107-12-0) → 2-methyl-3-(6-methylpyridin-3-yl)-3-oxopropanenitrile

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at 20℃;	80%

Methyl 6-methylnicotinate (5470-70-2) + methylmagnesium chloride (676-58-4) → 2-(6-methylpyridin-3-yl)propan-2-ol (40472-90-0)

Conditions	Yield
In tetrahydrofuran at -78℃; for 12h;	80%

Methyl 6-methylnicotinate (5470-70-2) + sodium 4-(methylthio)phenylacetate → 1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone (221615-72-1)

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h;	78.5%

Methyl 6-methylnicotinate (5470-70-2) + lithium (4-methylsulfonylphenyl)acetate (1421227-96-4) → 1-(6-methylpyridin-3-yl)-2-({4-[2-(6-methylpyridin-3-yl)-2-oxoethyl]phenyl}sulfonyl)ethanone (1421227-97-5) + 1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone (221615-75-4)

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1.5h;	A n/a B 78%

Methyl 6-methylnicotinate (5470-70-2) + ethyl acetate (141-78-6) → ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate (21683-58-9)

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -50℃; for 0.5h;	76%
With sodium hydride In N,N-dimethyl-formamide; toluene at 80℃; for 2.5h;

Methyl 6-methylnicotinate (5470-70-2) + 3-Trifluoromethylbenzaldehyde (454-89-7) → methyl 6-{(E)-2-[3-(trifluoromethyl)phenyl]ethenyl}nicotinate

Conditions	Yield
With zinc(II) chloride In acetic anhydride at 140℃; for 12h;	76%

Methyl 6-methylnicotinate (5470-70-2) + 5-Bromo-3,3-dihydroxy-1,3-dihydro-indol-2-one → 6-(5-Bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-ylmethyl)-nicotinic acid methyl ester

Conditions	Yield
at 120℃; for 4h;	75.9%

Methyl 6-methylnicotinate (5470-70-2) → methyl 6-(dibromomethyl)pyridine-3-carboxylate (1001200-43-6)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating;	75%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating;	75%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Heating / reflux;	19.4%

Methyl 6-methylnicotinate (5470-70-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → methyl 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-methyl-1,2-dihydropyridine-3-carboxylate (1360145-70-5)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine In benzene-d6 at 50℃; for 24h; Inert atmosphere; regioselective reaction;	75%
With P(C6H11)3; chloro(1,5-cyclooctadiene)rhodium(I) dimer In benzene-d6 ligand reacted with pinacolborane in C6D6 at 50°C for 24 h in presence of (Rh(C8H12)Cl)2 and P(C6H11)3; distilled;	75%

Methyl 6-methylnicotinate (5470-70-2) + 4-dimethylamino-benzaldehyde (100-10-7) → 6-[(E)-2-(4-Dimethylamino-phenyl)-vinyl]-nicotinic acid methyl ester

Conditions	Yield
With piperidine; acetic acid In toluene for 72h; Knoevenagel reaction; Heating;	74%

glyoxylic acid ethyl ester (924-44-7) + Methyl 6-methylnicotinate (5470-70-2) → (E)-methyl 6-(3-ethoxy-3-oxoprop-1-en-1-yl)nicotinate (1620675-63-9)

Conditions	Yield
In acetic anhydride at 130℃; for 48h;	73%
With acetic anhydride at 130℃; for 48h; Reflux;	73%
In acetic anhydride at 130℃; for 48h;	73%
With acetic anhydride at 130℃; for 48h;	57 g

Methyl 6-methylnicotinate (5470-70-2) + 2-(4-(methylthio)phenyl)acetic acid (16188-55-9) → 1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone (221615-72-1)

Conditions	Yield
With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h;	72%
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With tert-butylmagnesium chloride In tetrahydrofuran at 60℃; for 1h; Flow reactor; Stage #2: Methyl 6-methylnicotinate In tetrahydrofuran at 60℃; for 1h; Flow reactor; Stage #3: With hydrogenchloride In water; toluene Temperature; Flow reactor;

Upstream product

• 186581-53-3 diazomethane 
• 3222-47-7 6-methylnicotinic acid 
• 1121-78-4 5-Hydroxy-2-methylpyridine 
• 104-90-5 5-ethyl-2-methyl-pyridine 
• 67-56-1 methanol 
• 34107-46-5 6-methyl-3-pyridinemethanol 
• 1211000-51-9 (+/-)-(E)-methyl 3-(but-3-yn-2-yloxy)acrylate 
• 593-56-6 N-methoxylamine hydrochloride 
• 144-55-8 sodium hydrogencarbonate 
• 49668-89-5 5-(methoxycarbonyl)-2-methylpyridine 1-oxide 
• 922-67-8 propynoic acid methyl ester 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 676-58-4 methylmagnesium chloride 
• 1885-14-9 phenyl chloroformate 

Downstream Products

• 77629-49-3 5-(4,5-Dihydro-1H-pyrrol-2-yl)-2-methyl-pyridine 
• 6960-22-1 6-methylnicotinamide 
• 589-93-5 2,5-dimethylpyridine 
• 256935-78-1 2-methyl-indolizine-6-carboxylic acid 
• 1227917-62-5 (3R,6S)-3-methyl 1-(phenylmethyl) 6-methyl-1,3-piperidinedicarboxylate 

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