ChemicalBook CAS DataBase List QUINOXALINE-6-CARBALDEHYDE

QUINOXALINE-6-CARBALDEHYDE synthesis

11synthesis methods

Product Name:QUINOXALINE-6-CARBALDEHYDE
CAS Number:130345-50-5
Molecular formula:C9H6N2O
Molecular Weight:158.16

6344-72-5 Synthesis

6344-72-5
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$8.00/100mg

130345-50-5
159 suppliers
$24.00/100mg

Yield:130345-50-5 91%

Reaction Conditions:

with selenium(IV) oxide in 1,4-dioxane at 200; for 3 h;Product distribution / selectivity;Microwave irradiation;

Steps:

1.b
b) Quinoxaline-6-carbaldehyde. A suspension of 6-methylquinoxaline (8.0 g; 0.055 mol.) and selenium dioxide (6.77 g; 0.061 mol.) in 1,4-dioxane (5.0 mL) was irradiated at 200° C. for 30 min. in a Biotage Initiator microwave synthesizer. The above procedure was repeated five further times and the combined, cooled reaction mixtures were dissolved in CH₂Cl₂, filtered through a plug of celite, and concentrated in vacuo. Purification via flash column chromatography (silica gel, 20-50% ethyl acetate in hexanes) followed by crystallization from CH₂Cl₂provided quinoxaline-6-carbaldehyde (40.0 g, 91%) as a white solid. ¹H NMR (400 MHz, CDCl₃) δ ppm 10.25 (s, 1H) 8.95 (s, 2H) 8.57 (d, J=1.3 Hz, 1H) 8.24 (dd, J=8.6, 1.5 Hz, 1H) 8.20 (d, J=8.6 Hz, 1H). MS(ES+) m/e 159 [M+H]⁺.

References:

Duffy, Kevin J.;Fitch, Duke M.;Norton, Beth A. US2007/179144, 2007, A1 Location in patent:Page/Page column 4

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