106719-08-8|Ethyl 2-chloro-6-methoxyisonicotinate| Ambeed

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CAS No. :	106719-08-8
Formula :	C₉H₁₀ClNO₃
M.W :	215.63
SMILES Code :	O=C(OCC)C1=CC(OC)=NC(Cl)=C1
MDL No. :	MFCD14698195

Yield	Reaction Conditions	Operation in experiment
		Sulfuric acid (1 ml_) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 ml_). The clear solution is stirred at 700C for 18 h. The mixutre is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3x250 ml_). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 2-chloro-6-methoxy- isonicotinic acid ethyl ester (4.32 g) as a white solid; LC-MS: tR = 1.00 min, [M+1]+ = 215.89.
		a) Sulfuric acid (1 mL) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 70 C. for 18 h. The mixture is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3*250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> ethyl ester (4.32 g) as a white solid; LC-MS: tR=1.00 min, [M+1]+=215.89.
	With sulfuric acid; at 70℃; for 18h;	a) Sulfuric acid (1 mL) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 70 C. for 18 h. The mixture is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3*250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> ethyl ester (4.32 g) as a white solid; LC-MS: tR=1.00 min, [M+1]+=215.89.

3.205 g	With thionyl chloride; In toluene; at 0 - 20℃; for 24h;	Step 1 : Ethyl 2-chloro-6-methoxyisonicotinate To a previously sonicated suspension of <strong>[15855-06-8]2-chloro-6-methoxyisonicotinic acid</strong> (4.0g, 21 mmol) in ethanol (50 ml.) was added thionyl chloride (4.64 ml_, 64.0 mmol) at 0C. The reaction mixture was stirred at 0C for 2 h and then at room temperature for 18h. Thionyl chloride (4.64 ml_, 64.0 mmol) was slowly added and the mixture was stirred at room temperature for 4 h. The reaction mixture was quenched by slowly pouring into a saturated aqueous solution of sodium bicarbonate (200 ml_). Ice was added to the mixture to lower the temperature. The mixture was extracted with diethyl ether (150 ml_ x2). The combined organics were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford a clear syrup as crude product. The crude product was dried for 2 h under high vacuum while heating to 80C. The resulting residue was concentrated from toluene (500 ml.) to afford ethyl 2-chloro-6- methoxyisonicotinate as an off white solid (3.205 g). 1H NMR (400 MHz, CDCI3) delta 1.40 (s, 3H), 3.98 (s, 3H), 4.39 (s, 2H), 7.22 (s, 1 H), 7.44 (s, 1 H).
		Sulfuric acid (1 mL) is added to a suspension of <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> (4.16 g, 22.2 mmol) in ethanol (20 mL). The clear solution is stirred at 700C for 18 h. The mixutre is neutralised by adding sat. aq. NaHCO3 solution and then extracted three times with EA (3x250 mL). The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give <strong>[15855-06-8]2-chloro-6-methoxy-isonicotinic acid</strong> ethyl ester (4.32 g) as a white solid; LC-MS: tR = 1.00 min, [M+1]+ = 215.89.

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CAS No.: 106719-08-8

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CAS No.: 106719-08-8

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed