1-(4-PYRIDINYL)-1,3-BUTANEDIONE synthesis

5synthesis methods

Product Name:1-(4-PYRIDINYL)-1,3-BUTANEDIONE
CAS Number:75055-73-1
Molecular formula:C9H9NO2
Molecular Weight:163.17

2459-09-8 Synthesis

2459-09-8
287 suppliers
$7.00/10g

67-64-1
6 suppliers
$19.10/10ml

75055-73-1
36 suppliers
inquiry

Yield:75055-73-1 62%

Reaction Conditions:

Stage #1: 4-pyridinecarboxylic acid, methyl ester;propan-2-onewith sodium methoxide in diethyl ether; for 6 h;Heating / reflux;
Stage #2: with lithium hydroxide monohydrate;glacial acetic acid

Steps:

OO-1.1

Stepi: 1-Pyridin-4-ylbutane-1, 3-dione (oo-1); To a 500 mL flask with NaOMe (4.75 g) and anhydrous ether (130 mL) was sequentially added methyl isonicotinate (10.0 mL, 84.7 mmol), and a solution of acetone (12.4 mmol, 169 mmol) in ether {45 mL). The suspension was stirred at reflux for 6 hours, cooled, and filtered. The isolated solid was washed with ether and dissolved in water (40 mL). Glacial acetic acid (5.2 mL) was added and the mixture was extracted with chloroform (40 mL x 2). The organic extracts were dried over anhydrous Na₂SO₄ and concentrated to give the title compound oo-1 (8.6 g, 62% yield) as a brown solid, which was used without further purification. LCMS: 164.10 [M + H⁺]

References:

WO2008/17932,2008,A2 Location in patent:Page/Page column 92