5552-44-3|Diethyl pyridine-2,5-dicarboxylate| Ambeed

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Quality Control of [ 5552-44-3 ] Purity: 98% SDS Specification

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Product Details of [ 5552-44-3 ]

CAS No. :	5552-44-3
Formula :	C₁₁H₁₃NO₄
M.W :	223.23
SMILES Code :	O=C(C1=NC=C(C(OCC)=O)C=C1)OCC
MDL No. :	MFCD00145190
InChI Key :	AFWWHZBUQWEDLS-UHFFFAOYSA-N
Pubchem ID :	254728

Safety of [ 5552-44-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312-P330

Application In Synthesis of [ 5552-44-3 ]

* 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 [ 5552-44-3 ]

[ 5552-44-3 ] Synthesis Path-Downstream 1~35

1
[ 100-26-5 ]
[ 64-17-5 ]
[ 5552-44-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sulfuric acid; for 18.0h;Reflux;	Concentrated sulfuric acid (3.9 mL, 71.6 mmol) was added dropwise over 15 minutes to a stirred suspension of 2,5-pyridinedicarboxylic acid (3.0 g, 17.9 mol) in absolute ethanol (10 mL) and the resulting mixture heated to reflux for 18 hours. The solution was allowed to cool to room temperature and the solvents evaporated under reduced pressure. Saturated NaHCC>3 solution was added to the residue to adjust the pH to -8 then the aqueous phase was extracted with EtOAc (4 x 50 mL). The combined organic extracts were washed with brine (30 mL), dried (Na2S04) and evaporated under reduced pressure to leave the title compound (3.0 g, 75%) which was used without further purification.
67%	With sulfuric acid; for 4.0h;Reflux;	Diethyl pyridine-2,5-dicarboxylate (5.3)Pyridine-2,5-dicarboxylic acid (20.0 g, 120 mmol) was dissolved in ethanol (200 mL) and treated with concentrated solution of sulfuric acid (2.0 mL, 36 mmol) in ethanol (20 mL). The reaction was heated under reflux for 4hrs, concentrated and dissolved in EtOAc (10 mL). The mixture was washed with water (50mL), brine (50 mL), dried over sodium sulfate, filtered and evapourated to afford diethyl pyridine-2,5-dicarboxylate (18 g, 67 %). 1 H NMR (400MHz CDCI3) δΗ ppm 1 .25 (t, 3H), 4.3 (q, 2H), 8.2 (d, 1 H), 8.4 (d, 1 H), 9.4 (s, 1 H).
49%	With sulfuric acid; for 48.5h;Reflux;	To a suspension of 2, 5-pyridinedicarboxylic acid (20 g, 120 mmol) in absolute EtOH (120 ml_) was added cone. H2SO4 (25.6 ml_, 0.048 mmol) dropwise over a period of 30 min. The resulting reaction mixture was refluxed for 48 h. The reaction mixture was concentrated, and the resulting residue basified to pH 8 (sat. aq. NaHCCh). The resulting aqueous layer was extracted with EtOAC (4 x 200 ml_). The combined organic layers were washed with brine, washed, dried (Na2SC>4) and concentrated. Four other 20 g batches were reacted in parallel and the resulting crude material from each reaction was combined and purified by column chromatography on silica gel (60-120 mesh) eluting with 5% EtOAC/hexane to afford the title compound (65 g, 291 mmol, 49%).

	With thionyl chloride; triethylamine;	a) Add 50 mL of thionyl chloride to 25 g of pyridene-2,5-dicarboxylic acid and heat the so-formed mixture at reflux for 6 hrs. Remove all volatiles by vacuum distillation to obtain crude di acid chloride. Immerse flask contain diacid chloride in an ice-batch and add 100 mL of absolute ethanol thereto. Slowly add 30 mL of triethlamine to the stirred reaction mixture and continue stirring for 1/2 hr. Add Ethyl acetate/water to stirred reaction mixture and separate the organic layer. Remove the solvent to produce crude product. Re-crystallize crude product from hexane/methylene chloride to give 25 g of the pyridine-2,5-bis(ethylcarboxylate).
26.61 g	With sulfuric acid; In water; at 78℃; for 58.0h;	(0201) 2,5-pyridinedicarboxylic acid (25.08 g; 150 mmol) was added to ethanol (1,800 mL). Aqueous sulfuric acid (1.32 g) was added. The mixture was heated at reflux (about 78 C.) for 58 hours, during which time water was removed from the reaction. The reaction progress was monitored using NMR spectroscopy. After the 2,5-diethyl-2,5-pyridinedicarboxylate had been formed in >97% purity by NMR, the reaction mixture was allowed to cool to ambient temperature and was extracted with 2-methyltetrahydrofuran. The combined organic layers were washed with a saturated aqueous brine solution and deionised water, and dried (MgSO4). The organics were filtered and the volatiles were removed in vacuo to afford the title compound (26.61 g; 120 mmol; >99% conversion by GC).

References: [1]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 3025 - 3028.
[2]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 469 - 480.
[3]Dalton Transactions,2015,vol. 44,p. 15391 - 15395.
[4]European Journal of Organic Chemistry,2010,p. 174 - 182.
[5]CrystEngComm,2011,vol. 13,p. 2915 - 2922.
[6]Patent: WO2018/197714,2018,A1 .Location in patent: Page/Page column 115; 116.
[7]Liebigs Annalen der Chemie,1981,p. 2164 - 2179.
[8]Journal of Medicinal Chemistry,1983,vol. 26,p. 1282 - 1293.
[9]Patent: WO2013/72903,2013,A1 .Location in patent: Page/Page column 67.
[10]Patent: WO2021/58754,2021,A1 .Location in patent: Page/Page column 116-117.
[11]Zhurnal Prikladnoi Khimii,1959,vol. 32,p. 2820; engl. Ausg. S. 2904.
[12]European Journal of Medicinal Chemistry,2004,vol. 39,p. 889 - 895.
[13]Angewandte Chemie - International Edition,2015,vol. 54,p. 14570 - 14574.
Angew. Chem.,2015.
[14]Patent: US5350772,1994,A .
[15]Patent: US2018/148752,2018,A1 .Location in patent: Paragraph 0200-0201.

2
[ 100-26-5 ]
[ 5552-44-3 ]

References: [1]Arhiv za Kemiju,1946,vol. 18,p. 3,6.
Chem.Abstr.,1948,p. 3398.
[2]Synthesis,1999,p. 597 - 602.

3
[ 111-87-5 ]
[ 5552-44-3 ]
2-ethyl-5-octyl pyridinedicarboxylate [ No CAS ]
2-octyl-5-ethyl pyridinedicarboxylate [ No CAS ]
2,5-dioctyl pyridinedicarboxylate [ No CAS ]

References: [1]Tetrahedron,1994,vol. 50,p. 6999 - 7008.

4
[ 111-87-5 ]
[ 5552-44-3 ]
2-octyl-5-ethyl pyridinedicarboxylate [ No CAS ]

References: [1]Tetrahedron,1994,vol. 50,p. 6999 - 7008.

5
[ 5552-44-3 ]
[ 21514-99-8 ]

References: [1]Synthesis,1999,p. 597 - 602.
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 1282 - 1293.
[3]Angewandte Chemie - International Edition,2015,vol. 54,p. 14570 - 14574.
Angew. Chem.,2015.

6
[ 5552-44-3 ]
[ 17880-34-1 ]

Yield	Reaction Conditions	Operation in experiment
69%		5-(Ethoxycarbonyl)picolinic acid (5.4)To a stirring solution of <strong>[5552-44-3]diethyl pyridine-2,5-dicarboxylate</strong> (3.49 g, 15.6 mmol) in ethanol (31 ml) was added sodium hydroxide pellets (0.66 g, 16.6 mmol). The reaction was heated at reflux for 4 h. The reaction was quenched with 2M HCI (1 1 mL) at the reflux temperature, allowed to cool to room temperature and then 0 C. The resulting precipitate was filtered, washed with ethanol (25 mL) and dried with heating under vacuum to afford the mono-acid as a white free flowing powder (2.1 g, 69%). 1 H NMR (400MHz CDCI3) δΗ ppm 1 .25 (t, 3H), 4.35 (q, 2H), 8.15 (d, 2H), 8.46 (d, 2H), 9.18 (s, 1 H).

References: [1]European Journal of Organic Chemistry,2010,p. 174 - 182.
[2]Liebigs Annalen der Chemie,1981,p. 2164 - 2179.
[3]Patent: WO2013/72903,2013,A1 .Location in patent: Page/Page column 67.
[4]Chemistry - A European Journal,2003,vol. 9,p. 4924 - 4935.

7
[ 5552-44-3 ]
[ 35005-81-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 0℃; for 5.5h;	To a cooled (ice-bath) solution of diethyl pyridine-2, 5-dicarboxylate (10 g, 45 mmol) in a mixture of absolute EtOH (40 ml_) and THF (3.5 ml_) under nitrogen were added NaBH4 (4.26 g, 112 mmol) and anhydrous CaCh (7.86 g, 71 mmol) portion wise over 30 min. The resulting reaction mixture was stirred at 0C for 5 h. The reaction mixture was poured in sat. aq. NH4CI (150 ml_) and extracted with EtOAc (4 x 150 ml_). The combined organic extracts were dried Na2S04) and concentrated. Six other 10 g batches and one 5 g batch were reacted in parallel and the resulting crude material from each reaction was combined and purified by column chromatography with silica gel (60-120 mesh) eluting with 20% EtOAc/hexane to afford the title compound (55 g, 320 mmol, 100%).
84%	With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 0℃; for 12.0h;	To a stirred solution of 24 (2.50 g, 11.20 mmol) in EtOH (300.00 mL) and THF (275.00 mL), CaCl2 (4.97 g, 44.80 mmol) was added. The mixture was cooled to 0 C before adding NaBH4 (0.85 g, 22.40 mmol) portionwise. The reaction was stirred at 0 C for 12 h, then a saturated solution of NH4Cl was added and volatiles were removed under reduced pressure. The aqueous phase was extracted with DCM (3 x 25.00 mL) and the combined organic layers were dried over Na2SO4, filtered and evaporated. The crude was purified by means of chromatography on silica gel (25 % ethyl acetate in petroleum ether) to afford ethyl 6-(hydroxymethyl)nicotinate (84 % yield) as a transparent oil. ESI-MS m/z 182 [M+H]+, 204 [M+Na]+;1H NMR (300 MHz, CDCl3) δ1.41 (t, J = 7.1 Hz, 3H), 3.59 (br s, 1H), 4.42 (q, J = 7.1 Hz,2H), 4.83 (s, 2H), 7.35 (d, J = 8.1 Hz, 1H), 8.29 (d, J = 8.1 Hz, 1H), 9.17 (s, 1H). To a solution of the previously synthesize alcohol (1.70 g, 9.40 mmol) in dry DCM (30.00 mL), cooled to 0 C, SOCl2 (3.42 mL, 47.00 mmol) was added, and the reaction was stirred at 25 C for 2 h. A saturated solution of NaHCO3 was added and the aqueous phase was extracted with DCM (3 x 25.00 mL). The combined organic layers were dried overNa2SO4, filtered and evaporated to afford title compound(quantitative yield) as a yellow oil. ESI-MS m/z 200 [M+H]+, 222 [M+Na]+; 1H NMR (300 MHz, CDCl3) δ 1.41 (t, J = 7.1 Hz, 3H), 4.42 (q, J= 7.1 Hz, 2H), 4.73 (s, 2H), 7.59 (d, J = 8.1 Hz, 1H), 8.34 (dd, J= 8.1, 2.1 Hz, 1H), 9.16 (s, 1H).
66%	With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; for 3.0h;Inert atmosphere; Cooling with ice;	In an Ar atmosphere, calcium chloride (29.92 g, 269.6 mmol), ethanol (390 mL) and THF (390 mL) were introduced into a reactor, and subsequently sodium borohydride (20.40 g, 539.2 mmol) was introduced to the reactor in divided portions under ice cooling. After sodium borohydride was introduced, the reaction mixture was stirred for 2.5 hours under ice cooling. Compound T (30.09 g, 134.8 mmol) was introduced into the reaction mixture in divided portions under ice cooling, and the reaction mixture was stirred for 30 minutes under ice cooling. The reaction mixture was poured into ice water (1.5 L), and then ammonium chloride (300 g) was added to the reaction mixture with stirring. The target compound was extracted with ethyl acetate (1 L×2). The organic layer was washed sequentially with water (1 L) and saturated brine (1 L). The organic layer was dried over magnesium sulfate, and then the solvent of the organic layer was distilled off under reduced pressure. Thus, compound 9′ (16.12 g, yield 66.0%) as a pale yellow brown solid was obtained.

62%	With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0℃; for 1.0h;Inert atmosphere;	Sodium borohydride (1.27 g, 33.5 mmol) and anhydrous calcium chloride (2.35 g, 21.2 mmol) was added in several portions over 30 minutes to a stirred solution of <strong>[5552-44-3]diethyl pyridine-2,5-dicarboxylate</strong> (3.0 g, 13.4 mmol) in ethanol (12 mL) and THF (6 mL) at 0C under a nitrogen atmosphere. The mixture was allowed to warm to room temperature and stirring continued for one hour then poured into saturated NH4CI solution (150 mL) and extracted with EtOAc (5 x 50 mL). The combined organic extracts were dried (Na2S04) and evaporated under reduced pressure to leave a residue which was purified by column chromatography on silica gel (60- 120 mesh) using 36% EtOAc/hexanes as the eluent to give the title compound (1 .5 g, 62%) as an off-white solid.
45%	With sodium tetrahydroborate; calcium chloride; In ethanol; at -5℃; for 0.75h;	Example 51 Synthesis of Compound (II-9); Step (1): Compound 9a → Compound 9b; Compound 9a (12.8 g, 57.3 mmol) was dissolved in ethanol, and subsequently cooled to -5C. To the reaction solution was added sodium borohydride (1.41 g, 37.3 mmol), and then calcium chloride (4.14 g, 37.3 mmol) was added small-portion-wise, followed by stirring for 45 minutes. The reaction solution was poured into purified water (120 mL), and then ethanol was concentrated in vacuo. The precipitated solid was filtrated to yield Compound 9b (4.71 g, 45% yield). 1H-NMR (CDCl3) 8(delta): 9.16 (1H, d, J = 1.8 Hz), 8.29 (1H, dd, J = 1.8, 8.4 Hz), 7.35 (1H, d, J = 8.4 Hz), 4.83 (2H, br s), 4.42 (2H, q, J = 6.9 Hz), 3.69 (1H, s), 1.42 (3H, t, J = 6.9 Hz).
31.33 g (84%)	With sodium borohydrid; calcium chloride; In ethanol;	(a) Ethyl 6-hydroxymethylnicotinate. 45.77 g (205 mmol) of <strong>[5552-44-3]ethyl 2,5-pyridinedicarboxylate</strong> was dissolved in 410 ml of absolute ethanol in a one-liter round-bottomed flask. The reaction medium was cooled to -5 C. and 5.04 g (133.2 mmol) of sodium borohydride was added, followed by portionwise addition of 14.79 g (133.2 mmol) of calcium chloride, while keeping the temperature below -5 C. The reaction medium was stirred at -5 C. for two hours and poured into water. The product was extracted with ethyl ether and washed with water and the organic phase was then dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica eluted with ethyl ether, in order to obtain 31.33 g (84%) of a white crystalline solid.

References: [1]Patent: WO2021/58754,2021,A1 .Location in patent: Page/Page column 116; 117.
[2]Tetrahedron Letters,2016,vol. 57,p. 920 - 923.
[3]Dalton Transactions,2015,vol. 44,p. 15391 - 15395.
[4]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 3025 - 3028.
[5]CrystEngComm,2011,vol. 13,p. 2915 - 2922.
[6]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 469 - 480.
[7]Patent: US2015/225368,2015,A1 .Location in patent: Paragraph 0109; 0112; 0113.
[8]Patent: WO2018/197714,2018,A1 .Location in patent: Page/Page column 115-117.
[9]Patent: EP2341053,2011,A1 .Location in patent: Page/Page column 103-104.
[10]European Journal of Medicinal Chemistry,2004,vol. 39,p. 889 - 895.
[11]Patent: US6214878,2001,B1 .

8
[ 16110-09-1 ]
[ 64-17-5 ]
[ 201230-82-2 ]
[ 5552-44-3 ]
[ 128072-93-5 ]

References: [1]Heterocycles,1999,vol. 51,p. 2589 - 2602.

9
[ 5552-44-3 ]
[ 10177-23-8 ]

References: [1]European Journal of Medicinal Chemistry,2004,vol. 39,p. 889 - 895.
[2]Journal of Porphyrins and Phthalocyanines,2010,vol. 14,p. 469 - 480.
[3]Dalton Transactions,2015,vol. 44,p. 15391 - 15395.
[4]Tetrahedron Letters,2016,vol. 57,p. 920 - 923.

10
[ 5552-44-3 ]
[ 800371-97-5 ]