Home Cart Sign in  
Chemical Structure| 1721-26-2 Chemical Structure| 1721-26-2
Chemical Structure| 1721-26-2

Ethyl 2-methylnicotinate

CAS No.: 1721-26-2

4.5 *For Research Use Only !

Cat. No.: A107977 Purity: 98%

Change View

Size Price

US Stock

Global Stock

In Stock
1g łÇʶÊÊ Inquiry Inquiry
5g łÇÿ¶ÊÊ Inquiry Inquiry
10g łËÿ¶ÊÊ Inquiry Inquiry
25g łÍî¶ÊÊ Inquiry Inquiry
100g łÇîÿ¶ÊÊ Inquiry Inquiry

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1g

    łÇʶÊÊ

  • 5g

    łÇÿ¶ÊÊ

  • 10g

    łËÿ¶ÊÊ

  • 25g

    łÍî¶ÊÊ

  • 100g

    łÇîÿ¶ÊÊ

In Stock

- +

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of Ethyl 2-methylnicotinate

CAS No. :1721-26-2
Formula : C9H11NO2
M.W : 165.19
SMILES Code : CCOC(=O)C1=CC=CN=C1C
MDL No. :MFCD00006336
InChI Key :TZORNSWZUZDUCU-UHFFFAOYSA-N
Pubchem ID :74401

Safety of Ethyl 2-methylnicotinate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Ethyl 2-methylnicotinate

* 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 [ 1721-26-2 ]

[ 1721-26-2 ] Synthesis Path-Downstream   1~32

  • 2
  • [ 1721-26-2 ]
  • [ 50-00-0 ]
  • [ 106320-19-8 ]
  • 3
  • [ 1721-26-2 ]
  • [ 119-61-9 ]
  • [ 102024-16-8 ]
  • 4
  • [ 1721-26-2 ]
  • [ 99-61-6 ]
  • [ 105975-19-7 ]
  • 6
  • [ 1721-26-2 ]
  • [ 75-07-0 ]
  • [ 99357-77-4 ]
  • [ 99855-04-6 ]
  • 7
  • [ 1721-26-2 ]
  • [ 56826-61-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; diisobutylaluminium hydride; In tetrahydrofuran; hydrogenchloride; toluene; Step 1: To a stirred solution of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (1.50 g, 9.09 mmol) in freshly distilled THF (100 mL) at 0° C. was added diisobutylaluminum hydride (11.2 mL of a 1.5M solution in toluene, 16.9 mmol). The solution was stirred for 6 h at 0° C. and then warmed to ambient temperature. After 1 h, the solution was cooled in an ice bath and 1N HCl (75 mL) was added to quench the reaction. The mixture was made alkaline with aqueous NaOH (pH=8.5), filtered, and the solvents were concentrated under reduced pressure. The resulting aqueous solution was partitioned between CHCl3 and saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was washed with additional CHCl3 (5*40 mL). The organic layers were combined, dried (MgSO4), and evaporated under reduced pressure. 3-Hydroxymethyl-2-methylpyridine was obtained as a slightly amber oil and was used in the next step without purification (TLC: Rf =0.40 (5percent MeOH:CH2 Cl2)).
With sodium hydroxide; lithium aluminium tetrahydride; In tetrahydrofuran; water; ethyl acetate; Step 1. To a stirred solution of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (1.50 g, 9.09 mmol) in THF (65 mL) at 0° C. was added LAH (9.1 mL of a 1.0 M solution in THF; 9.1 mmol). The mixture was stirred at ambient temperature for 18 h and then quenched by the sequential addition of ethyl acetate (0.1 mL), water (0.1 mL), 15percent aqueous NaOH (0.1 mL) and water (0.28 mL). The solids were removed by filtration through celite and the filtrate solvents were removed under reduced pressure. 3-Hydroxymethyl-2-methylpyridine was obtained as an oil (TLC: Rf = 0.40 (5:95 MeOH:CH2 Cl2)).
  • 10
  • [ 1721-26-2 ]
  • [ 197079-01-9 ]
YieldReaction ConditionsOperation in experiment
98% With hydrazine hydrate; In ethanol; for 72h;Reflux; Inert atmosphere; To a solution of <strong>[1721-26-2]ethyl 2-methylnicotinate</strong> (500 mg, 3.0 mmol) in EtOH (2.3 mL) was added hydrazine monohydrate (0.3 mL, 6.1 mmol). The reaction mixture was heated at reflux for 3 days and then concentrated to afford the desired product as a beige solid (450 mg, 98percent). MS (ESI): mass calcd. for C7H9N3O, 151.1; m/z found, 152.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 9.57 (br s, 1H), 8.49 (dd, J=4.9, 1.8 Hz, 1H), 7.66 (dd, J=7.7, 1.7 Hz, 1H), 7.26 (ddd, J=7.7, 4.9, 0.5 Hz, 1H), 4.85-4.05 (bs, 2H), 2.50 (d, J=4.1 Hz, 3H).
  • 11
  • [ 164390-30-1 ]
  • [ 1721-26-2 ]
  • 12
  • [ 1721-27-3 ]
  • [ 1721-26-2 ]
  • 15
  • [ 1721-26-2 ]
  • [ 3182-95-4 ]
  • [ 153025-46-8 ]
  • 16
  • [ 1721-26-2 ]
  • [ 100-52-7 ]
  • [ 14578-18-8 ]
  • 20
  • [ 1721-26-2 ]
  • [ 1122-91-4 ]
  • [ 109270-10-2 ]
  • 24
  • [ 1721-26-2 ]
  • [ 63050-11-3 ]
  • 2-Dibromomethyl-nicotinic acid ethyl ester [ No CAS ]
  • 25
  • [ 1721-26-2 ]
  • [ 31181-61-0 ]
YieldReaction ConditionsOperation in experiment
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 24h;Inert atmosphere; To a solution of <strong>[1721-26-2]ethyl 2-methyl-3-pyridinecarboxylate</strong> (1.86 ml_, 12.1 mmol) in DCM (50 ml_) mCPBA was added (4.18 g, 24.2 mmol) at RT. The solution was stirred at RT for 24 hrs. The solution was filtered and concentrated. The residue was purified by FC on silica cartridge (eluent: from DCM to 10percent MeOH) to afford 3-(ethoxycarbonyl)-2-methylpyridin-N oxide (p231 , 2.23 g, y=quant). MS (m/z): 183.0 [MH]+
91% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; Preparation of Compound A22:To a solution of A21 (50.0 g, 0.303 mol) in DCM (200 mL) was added m-CPBA (80.0 g, 0.465 mol) at 0° C. After stirred at 0° C. for 1 hour at room temperature for overnight, the mixture was poured into ice water. 2N NaOH was added to adjust the pH to 8-9 and the resultant mixture was extracted with DCM (3.x.200 mL). The organic layer was dried over Na2SO4, filtered and concentrated to afford compound A22 (50.0 g, yield: 91percent) as a yellow solid.
91% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; Example 5f A21 A22 A23 A24 A25 A26 A27 [0431] Preparation of compound A22: To a solution of A21 (50.0 g, 0.303 mol) in DCM (200 mL) was added m-CPBA (80.0 g, 0.465 mol) at 0°C. After stirred at 0°C for 1 hour at room temperature for overnight, the mixture was poured into ice water. 2N NaOH was added to adjust the pH to 8-9 and the resultant mixture was extracted with DCM (3 x 200 mL). The organic layer was dried over Na2SC>4, filtered and concentrated to afford compound A22 (50. Og, yield: 91percent) as a yellow solid. [0432] Preparation of compound A23: The solution of A22 (50.0 g, 0.276 mmol) in acetic anhydride (300 mL) was heated to 90°C for 1.5 hour. Then the mixture was concentrated and the residue was poured into ice water; 2N NaOH was added to adjust the pH to 8-9 and the resultant mixture was extracted by ethyl acetate (3x 100 mL). The organic layer was dried over Na2SC>4 and concentrated to give the cured which was purified by chromatography on silica gel (petroleum ether / ethyl acetate = 5: 1) to afford the compound A23 (10.0 g, yield: 16percent) as a yellow oil. [0433] 1H NMR (400 MHz, CDC13): delta: 8.43 (d, J = 2.4 Hz, 1H), 7.99 (d, J = 1.6 Hz, 1H), 4.41-4.35 (q, J = 3.2 Hz, 3H), 2.83 (s, 3H), 2.34 (s, 3H), 1.42-4.39 (t, J = 3.2 Hz, 3H). [0434] Preparation of compound A24: To a solution of A23 (10.0 g, 44.8 mmol) in MeOH (300 mL) was added potassium carbonate (12.4 g, 89.8 mmol). After stirred at room temperature for 12 hour, the mixture was poured into ice water. 2N HC1 was added to adjust the pH to 8-9 and the mixture was extracted with ethyl acetate (2 x 100 mL). The organic layer was dried over Na2SC>4, filtered and concentrated to afford compound A24 (8.00 g, yield 99percent) as yellow solid. [0435] 1H NMR (400 MHz, DMSO-i 6): delta: 10.0 (s, 1H), 8.18 (d, J = 2.4 Hz, 1H), 7.54 (d, J =2.8 Hz, 1H), 4.32-4.26 (q, J = 3.2 Hz, 3H), 2.57(s, 3H), 1.33-1.29 (t, J = 3.2 Hz, 3H). [0436] Preparation of compound A25: To a solution of compound A24 (2.50 g, 13.8 mmol) in DCM (50 mL) was added imidazole (3.00 g, 44.1 mmol) and tert- Butyldimethylsilyl chloride (2.50 g, 16.7 mmol) and the mixture was stirred at room temperature for 3 hours. Then evaporated the solvent, the residue was purified by chromatography (petroleum ether/ethyl acetate = 5: 1) to give compound A25 (2.80 g, yield 69percent) as a yellow oil. [0437] 1H NMR (400 MHz, CDC13): delta: 8.12 (d, J = 2.8 Hz, 1H), 7.54 (d, J =2.8 Hz, 1H), 4.30-4.26 (q, J = 3.2 Hz, 3H), 2.64 (s, 3H), 1.32-1.28 (t, J = 3.2 Hz, 3H), 0.92 (s, 9H), 0.12 (s, 6H). [0438] Preparation of compound A26: To a solution of compound A25 (2.80 g, 9.48 mmol) in CC14 (100 mL) was added azodiisobutyronitrile (280 mg) and NBS (1.80 g, 10.1 mmol), the mixture was stirred at 70°C for 15 hours, then the solvent was evaporated, the residue was purified by chromatography (petroleum ether/ethyl acetate = 5: 1) to give compound A26 (1.60 g, yield 45percent) as a yellow oil. [0439] 1H NMR (400 MHz, CDC13): delta: 8.28 (d, J = 3.2 Hz, 1H), 7.68 (d, J =3.2 Hz, 1H), 4.98 (s, 3H), 4.45-4.40 (q, J = 3.2 Hz, 3H), 1.45-1.42 (t, J = 2.8 Hz, 3H), 1.00 (s, 9H), 0.26 (s, 6H). [0440] Preparation of compound A27: To a solution of compound A26 (1.60 g, 4.27 mmol) in EtOH (100 mL) was added the solution of methylamine in EtOH (1.24 g, 12.0 mmol, 30percentw/w) and the mixture was stirred at room temperature for 3 hour. Then the solvent was evaporated and the residue was purified by chromatography (petroleum ether/ethyl acetate = 5: 1) to give compound A27a (300 mg, yield: 25percent) as a yellow solid. [0441] 1H NMR (400 MHz, DMSO-i 6): delta: 8.34 (d, J = 2.8 Hz, 1H), 7.43 (d, J = 2.8 Hz, 1H), 4.42 (s, 2H), 3.06 (s, 3H), 0.95 (s, 9H), 0.20 (s, 6H). [0442] To a solution of compound A27a (300 mg, 1.14 mmol) in THF (5 mL) was added 6 N HCl (0.5mL). After stirred at room temperature for 1 hour, the mixture was concentrated to get compound A27 (150 mg, yield 80 percent) as a yellow solid. [0443] 1H NMR (400 MHz, DMSO-i 6): delta: 10.27 (s, 1H), 8.27 (d, J= 2.4 Hz, 1H), 7.32 (d, J =2.8 Hz, 1H), 4.37 (s, 2H), 3.0 (s, 3H). LCMS mobile phase: from 40percent water (0.05percent TFA) and 60percent CH3CN to 10percent water (0.05percent TFA) and 90percent CH3CN in 6 min, finally under these conditions for 0.5 min.] Purity is >95percent, Rt = 3.7 min; MS Calcd.: 164.1; MS Found: 165.1 ([M+l]+).
  • 26
  • [ 1721-26-2 ]
  • [ 931-20-4 ]
  • 3-[1-Hydroxy-1-(2-methyl-pyridin-3-yl)-meth-(Z)-ylidene]-1-methyl-piperidin-2-one [ No CAS ]
  • 27
  • [ 624-67-9 ]
  • [ 626-34-6 ]
  • [ 1721-26-2 ]
  • 28
  • [ 90643-19-9 ]
  • [ 1721-26-2 ]
  • 29
  • [ 60544-22-1 ]
  • [ 41867-20-3 ]
  • [ 1721-26-2 ]
  • [ 1149-24-2 ]
  • [ 632-93-9 ]
  • 30
  • [ 60544-22-1 ]
  • [ 21759-71-7 ]
  • [ 1721-26-2 ]
  • [ 1149-24-2 ]
  • [ 632-93-9 ]
  • 31
  • [ 60544-22-1 ]
  • [ 17469-21-5 ]
  • [ 1721-26-2 ]
  • [ 1149-24-2 ]
  • [ 632-93-9 ]
  • 32
  • [ 110-86-1 ]
  • [ 1721-26-2 ]
  • [ 58539-65-4 ]
 

Historical Records

Technical Information

Categories