[ CAS No. 30062-34-1 ]

Name: Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate
Brand: Ambeed
SKU: A119214
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2D3D

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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 30062-34-1 ]

CAS No. :	30062-34-1	MDL No. :	MFCD17015470
Formula :	C₇H₇NO₃	Boiling Point :	367.6±42.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	153.14	Pubchem ID :	12342664
Synonyms :

Computed Properties of [ 30062-34-1 ]

TPSA :Topological Polar Surface Area	55.4	H-Bond Acceptor Count :	3
XLogP3 :	0.3	H-Bond Donor Count :	1
SP3 :	0.14	Rotatable Bond Count :	2

Safety of [ 30062-34-1 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 30062-34-1 ]

Upstream synthesis route of [ 30062-34-1 ]
Downstream synthetic route of [ 30062-34-1 ]

[ 30062-34-1 ] Synthesis Path-Upstream 1~2

1
[ 67-56-1 ]
[ 19621-92-2 ]
[ 30062-34-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride In 1,4-dioxane at 20℃; for 48.00 h;	Step 1: Synthesis of methyl 6-hydroxypicolinate0OH MeOH. HCIrt,2dOHTo a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCI in dioxane (4N, 10 mL). The resulting mixture wasstirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid.
90%	With hydrogenchloride In 1,4-dioxane at 20℃; for 48.00 h;	To a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCl in dioxane (4N, 10 mL). The resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid.
90%	With hydrogenchloride In 1,4-dioxane at 20℃; for 48.00 h;	To a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCI in dioxane (4N, 10 mL). The resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid.

90%	With hydrogenchloride In 1,4-dioxane at 20℃; for 48.00 h;	To a solution of 6-hydroxypicolinic acid (13.0 g, 93.5 mmol) in methanol (150 mL) at room temperature was added HCl in dioxane (4N, 10 mL). The resulting mixture was stirred at room temperature for 48 hours. The reaction mixture was concentrated to give methyl 6-hydroxypicolinate (13 g, 90percent) as a white solid.
87%	for 20.00 h; Reflux	General procedure: 4-Hydroxypicolinic acid 3 (348 mg, 2.5 mmol) was added to methanol (25 mL), and then concentrated sulfuric acid (0.2 mL). The mixture was refluxed for 20 h, then the solvent was evaporated under vacuum. The residue was neutralized with saturated aqueous sodium bicarbonate solution, extracted with DCM/MeOH (10/1, 5×30 mL), dried over anhydrous Na₂SO₄, concentrated under vacuum to give compound 4 (196 mg, 51percent) as a white solid. ¹H NMR (400 MHz, Methanol-d₄) δ 7.92 (d, J = 7.0 Hz, 1H), 7.14 (s, 1H), 6.63 (d, J = 7.0 Hz, 1H), 3.99 (s, 3H). MS (ESI) m/z = 154.1 ([M+H]⁺). To a solution of compound 4 (77 mg, 0.5mmol) in DMF (2 mL) was added potassium carbonate (104 mg, 0.75 mmol), then 1,4-dibromobutane (325 mg, 1.5 mmol) at 0°C. The mixture was stirred at room temperature for 3 h, and then partitioned between water (30 mL) and ethyl acetate (EA, 30 mL). The organic phase was washed with water (3×30 mL), saturated brine (30 mL), dried over anhydrous Na₂SO₄, concentrated under vacuum, purified by column chromatography using DCM : MeOH (100:1) as eluent to give 5 (95 mg, 66percent) as a light yellow oil. ¹H NMR (400 MHz, DMSO-d₆) δ 8.51 (d, J = 5.6 Hz, 1H), 7.55 (d, J = 2.6 Hz, 1H), 7.22 (dd, J = 5.7, 2.6 Hz, 1H), 4.19 (t, J = 6.2 Hz, 2H), 3.62 (t, J = 6.5 Hz, 2H), 1.98 (p, J = 6.7 Hz, 2H), 1.92 – 1.83 (m, 2H). MS (ESI) m/z = 288.2 ([M+H]⁺). Corresponding arylpiperazine (arylpiperidine) (0.24 mmol), 5 (90 mg, 0.31 mmol), potassium carbonate (83 mg, 0.6mmol) and potassium iodide (40 mg, 0.24 mmol) were added to acetonitrile (5 mL). The reaction mixture was refluxed overnight, cooled to room temperature, partitioned between EA and water. The organic layer was dried over anhydrous Na₂SO₄, concentrated under vacuum to give 6a–6e which was used directly in the next step without further purification.
36%	at 65℃;	A solution of 6-hydroxypyridine-2-carboxylic acid (5.00 g, 35.94 mmol, 1.00 equiv) in methanol (100 mL) and sulfuric acid (20 mL). was stirred overnight at 65 °C. The resulting reaction mixture was concentrated under reduced pressure, diluted with water (200 mL) and the solid precipitate was collected by filtration and washed with water and aqueous NaHC0₃. The filter cake was dissolved in ethyl acetate (20 mL) dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 2 g (36percent) of the product as a white solid

Reference： [1] Patent: WO2004/37808, 2004, A1. Location in patent: Page 19-20
[2] Patent: WO2014/154727, 2014, A1. Location in patent: Page/Page column 38; 52
[3] Patent: US2014/296239, 2014, A1. Location in patent: Paragraph 0097; 0098
[4] Patent: WO2014/154726, 2014, A1. Location in patent: Page/Page column 38-39
[5] Patent: US2014/296296, 2014, A1. Location in patent: Paragraph 0106; 0107
[6] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 606 - 611
[7] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 722 - 748
[8] Patent: WO2013/96771, 2013, A1. Location in patent: Page/Page column 160
[9] Tetrahedron, 2010, vol. 66, # 7, p. 1483 - 1488
[10] Patent: WO2014/2057, 2014, A1. Location in patent: Page/Page column 72

2
[ 19621-92-2 ]
[ 30062-34-1 ]

Reference： [1] Biochemical Journal, 1950, vol. 46, p. 506

[ 30062-34-1 ] Synthesis Path-Downstream 1~10

1
[ 19621-92-2 ]
[ 30062-34-1 ]

Reference： [1]Biochemical Journal,1950,vol. 46,p. 506

3
[ 110-52-1 ]
[ 30062-34-1 ]
C₁₁H₁₄BrNO₃ [ No CAS ]