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Quality Control of [ 29682-14-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 29682-14-2 ]

CAS No. :	29682-14-2	MDL No. :	MFCD09062740
Formula :	C₇H₆N₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	182.13	Pubchem ID :	-
Synonyms :

Safety of [ 29682-14-2 ]

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Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
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Application In Synthesis of [ 29682-14-2 ]

* 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.

Upstream synthesis route of [ 29682-14-2 ]
Downstream synthetic route of [ 29682-14-2 ]

[ 29682-14-2 ] Synthesis Path-Upstream 1~3

1
[ 29682-14-2 ]
[ 35969-75-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With diisobutylaluminium hydride In dichloromethane; toluene at -78 - 20℃; for 3 h; Inert atmosphere	To a suspension of methyl 5-nitropicolinate (LIX) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78°C under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2x DCM, combined with the organic layer, dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5- nitropicolinaldehyde (LX) as a brown oil (0.64 g, 4.2 mmol, 60percent yield). 1H NMR (DMSO-d₆) 6 ppm 8.17 (d, J=9Hz, 1H), 8.81 (dd, J=9Hz, J=2Hz, 1H), 9.56 (d, J=2Hz, 1H), 10.08 (s, 1H).
60%	With diisobutylaluminium hydride In dichloromethane; toluene at -78 - 20℃; for 3 h; Inert atmosphere	Step 1 To a suspension of methyl 5-nitropicolinate (CX) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78° C. under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2*DCM, combined with the organic layer, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5-nitropicolinaldehyde (CXI) as a brown oil (0.64 g, 4.2 mmol, 60percent yield). ¹H NMR (DMSO-d₆) δ ppm 8.17 (d, J=9 Hz, 1H), 8.81 (dd, J=9 Hz, J=2 Hz, 1H), 9.56 (d, J=2 Hz, 1H), 10.08 (s, 1H).
60%	With diisobutylaluminium hydride In dichloromethane; toluene at -78 - 20℃; for 3 h; Inert atmosphere	To a suspension of methyl 5-nitropicolinate (LIX) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78°C under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2x DCM, combined with the organic layer, dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5-nitropicolinaldehyde (LX) as a brown oil (0.64 g, 4.2 mmol, 60percent yield). NMR (DMSO-d₆) δ ppm 8.17 (d, J=9Hz, 1H), 8.81 (dd, J=9Hz, J=2Hz, 1H), 9.56 (d, J=2Hz, 1H), 10.08 (s, 1H).

Reference： [1] Patent: WO2013/40215, 2013, A1, . Location in patent: Paragraph 00282
[2] Patent: US2015/266825, 2015, A1, . Location in patent: Paragraph 1336; 1337
[3] Patent: WO2018/75858, 2018, A1, . Location in patent: Paragraph 0314; 0315

2
[ 29682-14-2 ]
[ 67515-76-8 ]

Reference： [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 3342 - 3348
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 1, p. 47 - 52[4] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 1, p. 54 - 59
[5] Patent: US4638068, 1987, A,

3
[ 29682-14-2 ]
[ 1072103-29-7 ]

Reference： [1] Patent: US2011/111046, 2011, A1,
[2] Patent: WO2011/58473, 2011, A1,

[ 29682-14-2 ] Synthesis Path-Downstream 1~6

1
[ 29682-14-2 ]
[ 67515-76-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h;	Compound 24C (500 mg, 2.74 mmol) was dissolved in methanol (30 mL).Add 10% Pd/C, hydrogenate at room temperature for 2 h. Then filter.Concentrated to give compound 24D (400 mg, 96% yield).
	In ethyl acetate;	EXAMPLE 60 Preparation of methyl 5-aminopicolinate STR223 A solution containing 10 g methyl 5-nitropicolinate in 400 ml ethyl acetate is stirred under hydrogen in the presence of 1 g platinum oxide at room temperature and atmospheric pressure. When no further hydrogen uptake occurs, the catalyst is removed by filtration, the filtrate concentrated, and the product collected. This is recrystallized from ethyl acetate to give analytically pure methyl 5-aminopicolinate, mp 147-150.5 C.

Reference： [1]Patent: CN104045552,2019,B .Location in patent: Paragraph 0299; 0300; 0307; 0308
[2]Journal of the American Chemical Society,2009,vol. 131,p. 3342 - 3348
[3]Chemistry of Heterocyclic Compounds,1990,vol. 26,p. 47 - 52
Khimiya Geterotsiklicheskikh Soedinenii,1990,p. 54 - 59
[4]Patent: US4638068,1987,A

2
[ 67-56-1 ]
[ 30651-24-2 ]
[ 29682-14-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	for 16h;Reflux;	Compound 24B (1 g, 6 mmol) was dissolved in methanol (50 mL).The reaction solution was heated to reflux for 16 hours. Adjust pH = 8-9 with 1M sodium hydroxide,Extract with ethyl acetate and dry,Concentration gave compound 24C (1 g, 98percent yield).
94%	With hydrogenchloride; for 16h;Heating / reflux;	Step 3: A suspension of <strong>[30651-24-2]5-nitropicolinic acid</strong> (6.0 g, 36 mmol) in methanolic HCI (1.25 M) was heated to reflux and stirred for 16 hours. The mixture was cooled to ambient temperature. The product was filtered and rinsed with additional methanol (20 mL) and dried under vacuum, providing 6.1 g of methyl 5-nitropicolinate, in 94% yield; 1H NMR (DMSCW) delta 3.95 (s, 3H), 8.29 (dd, 1 H, J = 8.4 Hz, J = 0.6 Hz), 8.75 (dd, IH, J = 8.4 Hz, J = 2.7 Hz), 9.46 (dd, IH, J = 2.7 Hz, J = 0.6 Hz).
89%		5-Nitropyridine-2-carboxylic acid (100 g, 0.60 mol) was heated at reflux in methanol (1 L) and sulfuric acid (57 mL) for 5 hours. The reaction mixture was cooled, reduced to half volume in vacuo, and the residue neutralized with a solution of sodium carbonate. The resulting precipitate was filtered to give methyl 5-nitropyridine-2-carboxylate (yield 89%, 98

	With sulfuric acid; for 5h;Reflux;	5-Nitropyridine-2-carboxylic acid (100 g, 0.60 mol) was heated at reflux in methanol (1 L) and sulfuric acid (57 ml_) for 5 hours. The reaction mixture was cooled, reduced to half volume in vacuo, and the residue neutralized with a solution of sodium carbonate. The resulting precipitate was filtered to give methyl 5-nitropyridine-2-carboxylate (yield 89%, 98 g).
	With sulfuric acid;Inert atmosphere; Reflux;	General procedure: Synthesis of methyl ester derivatives of M6, M7, and M17 was carried out under catalytic esterification conditions as depicted in Scheme 1. To a solution of the appropriate carboxylic acid in methanol few drops of conc. sulfuric acid were added. Subsequently, the reaction mixture was refluxed for 6-10 h. After completion, the volatile solvents were evaporated under reduced pressure and the residue was dissolved in water/ethyl acetate mixture. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with 5% sodium bicarbonate, brine, and was dried over anhydrous sodium sulfate. After filtration the desired ester was obtained using flash column chromatography.

Reference： [1]Patent: CN104045552,2019,B .Location in patent: Paragraph 0299; 0300; 0305; 0306
[2]Patent: WO2008/27542,2008,A2 .Location in patent: Page/Page column 74
[3]Patent: US2011/111046,2011,A1 .Location in patent: Page/Page column 15
[4]Patent: WO2011/58473,2011,A1 .Location in patent: Page/Page column 29
[5]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2950 - 2956

3
[ 25697-57-8 ]
[ 29682-14-2 ]
[ 64215-07-2 ]

Yield	Reaction Conditions	Operation in experiment
	In <i>N</i>-methyl-acetamide	9 EXAMPLE 9 EXAMPLE 9 To the stirred suspension of 1.73 g of sodium hydride in 30 ml of dimethylformamide the solution of 12.7 g of m-chlorobenzylmercaptan is added during 2 minutes and stirring is continued for 15 minutes. Thereupon the solution of 12.25 g of 5-nitro-pyridine-2-carboxylic acid methyl ester in 75 ml of dimethylformamide is added all at once. The mixture is stirred for 1 hour on the steam bath and allowed to stand at room temperature overnight. It is poured onto ice and acetic acid, the suspension obtained filtered and the residue recrystallized from 95% aqueous ethanol, to yield the 5-(m-chlorobenzylmercapto)-2-pyridinecarboxylic acid methyl ester melting at 75°-77°.
	In <i>N</i>-methyl-acetamide	2 EXAMPLE 2 The starting material is prepared as follows: To the stirred suspension of 1.73 g of sodium hydride in 30 ml of dimethylformamide the solution of 12.7 g of m-chlorobenzylmercaptan is added during 2 minutes and stirring is continued for 15 minutes. Thereupon the solution of 12.25 g of 5-nitro-pyridine-2-carboxylic acid methyl ester in 75 ml of dimethylformamide is added all at once. The mixture is stirred for 1 hour on the steam bath and allowed to stand at room temperature overnight. It is poured onto ice and acetic acid, the suspension obtained filtered and the residue recrystallized from 95% aqueous ethanol, to yield the 5-(m-chlorobenzylmercapto)-2-pyridinecarboxylic acid methyl ester melting at 75°-77°.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US4197302, 1980, A Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US4202901, 1980, A
[2]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US4036965, 1977, A

4
[ 29682-14-2 ]
[ 1072103-29-7 ]

Reference： [1]Patent: US2011/111046,2011,A1
[2]Patent: WO2011/58473,2011,A1

5
[ 29682-14-2 ]
[ 35969-75-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 20℃; for 3h;Inert atmosphere;	To a suspension of methyl 5-nitropicolinate (LIX) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78C under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2x DCM, combined with the organic layer, dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5- nitropicolinaldehyde (LX) as a brown oil (0.64 g, 4.2 mmol, 60% yield). 1H NMR (DMSO-d6) 6 ppm 8.17 (d, J=9Hz, 1H), 8.81 (dd, J=9Hz, J=2Hz, 1H), 9.56 (d, J=2Hz, 1H), 10.08 (s, 1H).
60%	With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 20℃; for 3h;Inert atmosphere;	Step 1 To a suspension of methyl 5-nitropicolinate (CX) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78 C. under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2*DCM, combined with the organic layer, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5-nitropicolinaldehyde (CXI) as a brown oil (0.64 g, 4.2 mmol, 60% yield). 1H NMR (DMSO-d6) delta ppm 8.17 (d, J=9 Hz, 1H), 8.81 (dd, J=9 Hz, J=2 Hz, 1H), 9.56 (d, J=2 Hz, 1H), 10.08 (s, 1H).
60%	With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 20℃; for 3h;Inert atmosphere;	To a suspension of methyl 5-nitropicolinate (LIX) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78C under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2x DCM, combined with the organic layer, dried over MgS04, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5-nitropicolinaldehyde (LX) as a brown oil (0.64 g, 4.2 mmol, 60% yield). NMR (DMSO-d6) delta ppm 8.17 (d, J=9Hz, 1H), 8.81 (dd, J=9Hz, J=2Hz, 1H), 9.56 (d, J=2Hz, 1H), 10.08 (s, 1H).

60%

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 20℃; for 3h;Inert atmosphere;

To a suspension of methyl 5-nitropicolinate (CII) (1.282 g, 7.03 mmol) in DCM (25 mL) stirred at -78 C. under argon was slowly added DIBAL (1M in toluene) (9.14 mL, 9.14 mmol). The solution was allowed to warm to room temperature over 3 h. An aqueous solution of potassium sodium tartrate was added, diluted further with water and DCM. The solution was stirred at room temperature for another 30 min before the organic layer was separated. The aqueous layer was extracted 2*DCM, combined with the organic layer, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography to produce 5-nitropicolinaldehyde (CIII) as a brown oil (0.64 g, 4.2 mmol, 60% yield). 1H NMR (DMSO-d6) delta ppm 8.17 (d, J=9 Hz, 1H), 8.81 (dd, J=9 Hz, J=2 Hz, 1H), 9.56 (d, J=2 Hz, 1H), 10.08 (s, 1H).

Reference： [1]Patent: WO2013/40215,2013,A1 .Location in patent: Paragraph 00282
[2]Patent: US2015/266825,2015,A1 .Location in patent: Paragraph 1336; 1337
[3]Patent: WO2018/75858,2018,A1 .Location in patent: Paragraph 0314; 0315
[4]Patent: US2019/263821,2019,A1 .Location in patent: Paragraph 0754

6
[ 29682-14-2 ]
[ 107504-07-4 ]

Reference： [1]Patent: US4638068,1987,A

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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

[ CAS No. 29682-14-2 ] {[proInfo.proName]}

Quality Control of [ 29682-14-2 ]

Related Doc. of [ 29682-14-2 ]

Product Details of [ 29682-14-2 ]

Safety of [ 29682-14-2 ]

Application In Synthesis of [ 29682-14-2 ]

[ 29682-14-2 ] Synthesis Path-Upstream 1~3

[ 29682-14-2 ] Synthesis Path-Downstream 1~6

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry