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[ CAS No. 626-34-6 ] {[proInfo.proName]}

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Chemical Structure| 626-34-6

Chemical Structure| 626-34-6

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Quality Control of [ 626-34-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 626-34-6 ]

CAS No. :	626-34-6	MDL No. :	MFCD02730138
Formula :	C₆H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YPMPTULBFPFSEQ-PLNGDYQASA-N
M.W :	129.16	Pubchem ID :	643756
Synonyms :

Safety of [ 626-34-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 626-34-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 626-34-6 ]

[ 626-34-6 ] Synthesis Path-Downstream 1~19

1
[ 5444-80-4 ]
[ 626-34-6 ]
[ 1721-26-2 ]

Reference： [1]Chemische Berichte,1949,vol. 82,p. 216
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 897 - 900
[3]Chemische Berichte,1949,vol. 82,p. 216

2
[ 626-34-6 ]
[ 13395-36-3 ]
6-<i>tert</i>-butyl-2-methyl-pyridine-3,4-dicarboxylic acid diethyl ester [ No CAS ]

Reference： [1]Chemische Berichte,1921,vol. 54,p. 732

3
[ 626-34-6 ]
[ 13395-36-3 ]
3-(1-amino-ethylidene)-2-(3,3-dimethyl-2-oxo-butyl)-2-hydroxy-succinic acid diethyl ester [ No CAS ]

Reference： [1]Chemische Berichte,1921,vol. 54,p. 732

4
[ 626-34-6 ]
[ 107-02-8 ]
[ 1721-26-2 ]

Reference： [1]Journal of Organic Chemistry,1956,vol. 21,p. 800
[2]Journal of Heterocyclic Chemistry,1991,vol. 28,p. 1315 - 1324
[3]Journal of the Chemical Society. Perkin transactions I,1984,p. 1501 - 1505

5
[ 624-67-9 ]
[ 626-34-6 ]
[ 1721-26-2 ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 879 - 887

6
[ 720-94-5 ]
[ 626-34-6 ]
2-Methyl-6-p-tolyl-4-trifluoromethyl-nicotinic acid ethyl ester [ No CAS ]

Reference： [1]Synthesis,1997,p. 1321 - 1324

7
[ 626-34-6 ]
[ 1721-26-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849
[2]Chemische Berichte,1957,vol. 90,p. 2265,2270

8
[ 626-34-6 ]
[ 37669-78-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1841 - 1849
[2]Journal of Organic Chemistry,1956,vol. 21,p. 800

9
dimethyl dihydropyridine [ No CAS ]
diethyl dihydropyridine [ No CAS ]
[ 626-34-6 ]
[ 6334-18-5 ]
[ 72509-76-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	In hexane; isopropyl alcohol;	Step B. Synthesis of Felodipine In a four necked, 3 liter flask, a solution of MBI (about 268.4 g, 0.98 mole) in isopropanol was brought to reflux and a solution of ethyl 3-aminocrotonate (about 114.2 g, 0.8 mole) in isopropanol was added at such a rate to maintain the internal temperature at about 81-83 C. and refluxed for about 1 hour. The temperature of the reaction was then lowered to about 40-50 C. and excess isopropanol removed under reduced pressure maintaining the internal temperature at about 40-45 C. to furnish a viscous yellow orange residue. LC analysis of this residue indicated about 75% felodipine product, 13% MBI, 4% dichlorobenzaldehyde and about 0.5% symmetrical dimethyl dihydropyridine analog and about 0.4% diethyl dihydropyridine analog. Hexane was added to the residue and the suspension stirred under reflux for about 1 hr. The temperature was allowed to fall to about 40 C. during which solids formed. The solids were filtered and washed with fresh hexane and dried to yield felodipine in about 62% yield. LC analysis indicated about 92.8% purity of felodipine.

Reference： [1]Patent: US5977369,1999,A

10
[ 626-34-6 ]
[ 96516-25-5 ]
[ 96516-29-9 ]
3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl ethyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol;	EXAMPLE 19 Synthesis of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl ethyl 2,6-dimethyl-4-(2-fluoro-3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (162) A mixture of 184 mg of <strong>[96516-29-9]2-fluoro-3-nitrobenzaldehyde</strong>, 324 mg of 3-(N-benzyl-N-methylamino)-2,2-dimethylpropyl acetoacetate and 138 mg of ethyl 3-aminocrotonate in 1 ml of 2-propanol was reacted and then purified in the same way as in Example 8 to yield 120 mg of the desired compound (162). IR (CHCl3) numaxcm-1: 1680, 1348, 1096 NMR (CDCl3) deltappm: 7.8-6.8 (m, 8H), 6.35 (brs, 1H), 5.27 (s, 1H), 4.00 (q, 2H, J=7 Hz), 3.84 (s, sH), 3.39 (s, 2H), 2.25 (s, 8H), 2.03 (s, 3H), 1.18 (t, 3H, J=7 Hz), 0.85 (s, 6H),

Reference： [1]Patent: US4578395,1986,A

11
[ 110-89-4 ]
[ 626-34-6 ]
[ 107-02-8 ]
[ 1721-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; hydrogen sulfide; In chloroform; isopropyl alcohol;	EXAMPLE 1 Ethyl 2-methylnicotinate STR6 To a mixture of 800 ml. of ethyl 3-aminocrotonate, 30 ml. of piperidine and 1.4 l. of isopropanol, stirred at 25°-30° C., 540 ml. of acrolein were added slowly over a 2 hour period with stirring. Upon completion of the addition of the acrolein, the reaction mixture was heated to reflux and refluxed for 31/2 hours. Then the reaction mixture was evaporated at reduced pressure to dryness. The residue was heated to 100° C. and 610 g. of sulfur were added thereto portionwise. The reaction mixture was then heated at 100° C. for 2 hours and at 125° C. for 11/2 hours. The reaction mixture was allowed to cool to about room temperature and 1 l. of chloroform was added thereto. The reaction mixture was filtered through Celite and the filter cake was washed with additional chloroform. The combined chloroform filtrate and washings were extracted three times with 1 l. portions of 2 N. hydrochloric acid. The aqueous acidic layers were combined and, with cooling, were made basic with 2 N. sodium hydroxide solution. The obtained aqueous basic solution was extracted three times with 1 l. portions of chloroform. The chloroform extracts were combined, washed with saturated brine, dried over anhydrous sodium sulfate and evaporated at reduced pressure to obtain an oily residue which was distilled under high vacuum to obtain the pure product (350 g.), b.p. 73°-77° C./0.5 mm. Hg.

Reference： [1]Patent: US4329349,1982,A

12
[ 626-34-6 ]
[ 188869-05-8 ]
[ 1075257-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; at 80℃; for 24h;	Example 1 : 5-tert-butyl 3-ethyl 2-methyl-6,7-dihydro-lH-pyrrolo[3,2-c]pyridine-3,5(4H)- dicarboxylateA mixture of tert-butyl 3-bromo-4-oxopiperidine-l-carboxylate (3.0 g), (Z)- ethyl 3-aminobut-2-enoate (6.8 mL), and sodium bicarbonate (1.1 g) was heated to 80°C for 24 hours. The reaction was cooled to room temperature and diluted with ethyl acetate and water. The aqueous phase was extracted twice with ethyl acetate. The combined organics were dried over anhydrous magnesium sulfate and concentrated.Excess (Z)-ethyl 3-aminobut-2-enoate was removed via distillation and the resulting residue was purified by column chromatography on silica gel (1 : 2 = ethyl acetate: hexanes) to obtain the title compound (0.73 g) having the following physical data. 1H NMR (CDCl3): delta 7.87 (bs, IH), 4.55 (s, 2H), 4.25 (q, J = 7.1 Hz, 2H), 3.76-3.60 (m,2H), 2.66-2.54 (m, 2H), 2.51 (s, 3H), 1.47 (s, 9H), 1.34 (t, J = 7.2 Hz, 3H);Mass data (ESI, Pos.): m/z 331 (M + Na)+.

Reference： [1]Patent: WO2008/134354,2008,A1 .Location in patent: Page/Page column 59

13
[ 626-34-6 ]
[ 72509-76-3 ]

Reference： [1]Tetrahedron,2011,vol. 67,p. 10222 - 10228

14
[ 626-34-6 ]
[ 68064-69-7 ]
[ 72509-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 25 - 30℃; for 11h;Product distribution / selectivity;	Methyl ester of 2,3-dichloro-benzylidiene intermediate (50.0 g, 0.18 mol) was charged in a well equipped reaction assembly followed by the addition of ethyl-3-amino crotonate (28.5 g, 0.22 mol) at 25- 30C.Reacton mass was stirred at same temperature with simultaneous monitoring of the reaction for 11 hours. This reaction mass was then charged with (150 ml toluene) and 150 ml of heptane under stirring at 25-30C. Contents were cooled to 10-15C for another 30 minutes. Felodipine so obtained was filtered off washed with mixture of methyl tert-butyl ether and heptanes. Felodipine was dried under vacuum. Yield obtained was: 58 g with HPLC purity of 98.5%.

Reference： [1]Patent: WO2012/123966,2012,A1 .Location in patent: Page/Page column 29

15
[ 626-34-6 ]
[ 107-18-6 ]
[ 1721-26-2 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 7926 - 7928

16
[ 74073-22-6 ]
[ 626-34-6 ]
[ 72509-76-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 90℃; for 0.15h;Microwave irradiation;	General procedure: A mixture of the aldehyde 1 (2 mmol), the 1,3-dicarbonyl compound 2 (2 mmol) and the 3D printed Al2O3 structure (0.350 g) was submitted to microwave irradiation (120 C) for in coated vial. Once the aldehyde component was consumed (TLC control) the corresponding 3-aminocrotonate 6 (2 mmol) was added and the mixture heated at 90 C (microwave irradiation). After completion of the reaction, as indicated by TLC, the mixture was cooled and the desired compound solidified. For those 1,4-dihydropyridines that not solidified, the reaction mixture was poured onto crushed ice and stirred for 5-10 min. The solid obtained was filtered under suction, washed with ice-cold water (20 mL) and then purified by column chromatography or recrystallization from the appropriate solvent.

Reference： [1]Applied Catalysis A: General,2017,vol. 530,p. 203 - 210

17
[ 626-34-6 ]
[ 105-45-3 ]
[ 6334-18-5 ]
[ 72509-76-3 ]

Yield	Reaction Conditions	Operation in experiment
94.3%		20.0-dichlorobenzaldehyde 70.0 g (0.40 mol), beta-aminocrotonate ethyl ester in a 500 mL round bottom flask55.8g (0.48mol),62.0 g (0.48 mol) of methyl acetoacetate, followed by 4.5 g (0.053 mol) of piperidine and 4.2 g (0.053 mol) of pyridine.The heating was started slowly and the temperature was raised. The reaction was maintained at 75-80 C for 9 h, and 200 g of absolute ethanol was added while heating, and the mixture was heated to reflux for 1 h, and filtered while hot.The mixture was cooled to 15 C and stirred for 1 h, and suction filtered. The filter cake was washed with a small amount of dry ethanol and dried to give 145 g of pale yellow solid.Yield: 94.3%, purity 99.1%

Reference： [1]Patent: CN108840819,2018,A .Location in patent: Paragraph 0014; 0040-0042; 0045-0048; 0051-0053

18
[ 80370-42-9 ]
[ 626-34-6 ]
[ 13602-96-5 ]

Yield	Reaction Conditions	Operation in experiment
32 g		To a mixture of <strong>[80370-42-9]ethyl 2-formyl-3-oxopropanoate</strong> (50.0 g) and diethyl ether (350 mL) was added dropwise TEA (38.5 g) at - 10°C. The reaction mixture was stirred at 25°C for 2 hr. The solvent was evaporated under reduced pressure, and a solution of 4-methylbenzenesulfonyl chloride (72.9 g) in DMF (200 mL) was added thereto with stirring at -20°C. The reaction mixture was warmed to 25°C, and stirred for 4 hr. To the mixture was added a solution of ethyl (2Z) -3-aminobuta-2-enoate (47.1 g) and pyridine (109 g) in DMF (150 mL) at 25°C. The reaction mixture was stirred at 80°C for 10 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with saturated aqueous sodium hydrogencarbonate solution (500 mL), and the mixture was extracted with ethyl acetate (600 mL x 2). The combined organic layer was washed with saturated brine (1000 mL x 2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (32.0 g). MS: [M+H]+237.9.

Reference： [1]Patent: WO2019/27054,2019,A1 .Location in patent: Paragraph 0381

19
[ 80370-42-9 ]
[ 626-34-6 ]
[ 13602-96-5 ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl 2-formyl-3-oxopropanoate (500.0 g) was dissolved in DMF (1.50 L) , and the solution was cooled to 0°C. To the solution were added TEA (702.0 g) and 4-methylbenzenesulfonyl chloride (728.0 g) at 0°C, and the mixture was stirred under nitrogen atmosphere at 15°C for 1 hr. To the mixture were added molecular sieve 4A (500.0 g) , pyridine (1.10 kg) and a solution of ethyl 3-aminobuta-2-enoate (448 g) in DMF (1 L) at 15°C, and the mixture was stirred at 80°C under nitrogen atmosphere for 12 hr. The same procedure was carried out a total of ten times in parallel, all the mixtures were cooled to 15°C, the mixtures were combined, and the solid was removed by filtration. The filtrate was poured into saturated aqueous sodium hydrogencarbonate solution (50 L) , and the mixture was extracted with tert-butyl methyl ether (20 L and 10 L) . The combined organic layers were washed with saturated brine (10 L) , dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue was added petroleum ether (5 L) , the mixture was stirred, and the precipitated solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (2.50 kg). XH NMR (400 MHz, DMSO-d6) delta 1.32-1.36 (6H, m) , 2.79 (3H, s) , 4.33-4.39 (4H, m) , 8.55 (1H, d, J = 1.6 Hz), 9.08 (1H, d, J = 2.0 Hz) .

Reference： [1]Patent: WO2019/27054,2019,A1 .Location in patent: Paragraph 0427

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Technical Information

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Historical Records

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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
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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