ChemicalBook CAS DataBase List 2-Pyridinecarboxylicacid,5-methyl-,methylester(9CI)

2-Pyridinecarboxylicacid,5-methyl-,methylester(9CI) synthesis

11synthesis methods

Product Name:2-Pyridinecarboxylicacid,5-methyl-,methylester(9CI)
CAS Number:29681-38-7
Molecular formula:C8H9NO2
Molecular Weight:151.16

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

589-93-5 Synthesis

589-93-5
131 suppliers
$32.00/5mL

2-Pyridinecarboxylicacid,5-methyl-,methylester(9CI)

29681-38-7
110 suppliers
$13.00/100mg

Yield: 50%

Reaction Conditions:

Stage #1:2,5-dimethylpyridine with selenium(IV) oxide in pyridineReflux;
Stage #2:methanol with sulfuric acid for 5 h;Reflux;

Steps:

20.6
Intermediate 20-6: Methyl 5-methylpyridine-2-carboxylateTo a solution of 2,5-dimethylpyridine (3.00 g, 28.0 mmol, CAS 589-93-5) in pyridine (15 mL) was added selenium dioxide (4.66 g, 42.0 mmol, CAS 7446-08-4). The reaction mixture was heated at reflux overnight. After cooling to RT a solid was filtered off and washed with water and pyridine (2x5 mL/wash). The filtrate was evaporated and the crude retaken in methanol (100 mL). Sulphuric acid (1.34 mL, 25.0 mmol) was added and the reaction mixture was heated at reflux for 5 h. After cooling to RT the reaction mixture was basified with 20% NaOH (aq). The methanol was evaporated off and water was added (50 mL). This mixture was extracted with DEE (3 x 100 mL). The combined organics were dried (Na₂SO₄) and evaporated to afford the title compound (2.11 g, 50 %) as light-brown oil.¹H NMR (400 MHz, CDCl₃) δ 2.40 (s, 3H), 3.97 (s, 3H), 7.61 (d, IH), 8.01 (d, IH), 8.54 (s, IH).

References:

ASTRAZENECA AB;ASTRAZENECA UK LIMITED WO2009/81195, 2009, A1 Location in patent:Page/Page column 84

67-56-1 Synthesis

67-56-1
745 suppliers
$7.29/5ml-f