ChemicalBook CAS DataBase List 4-METHOXYPICOLINALDEHYDE

4-METHOXYPICOLINALDEHYDE synthesis

12synthesis methods

Product Name:4-METHOXYPICOLINALDEHYDE
CAS Number:16744-81-3
Molecular formula:C7H7NO2
Molecular Weight:137.14

16665-38-6

16744-81-3

The general procedure for the synthesis of 4-methoxypyridin-2-aldehyde from (4-methoxypyridin-2-yl)methanol was as follows: - Manganese(IV) oxide (2.412 mL, 139.42 mmol, 4 eq.) was added batchwise to a solution of (4-methoxypyridin-2-yl)methanol (4.85 g, 34.85 mmol, 1 eq.) in ethyl acetate (150 mL). - The reaction mixture was stirred at 80 °C for 2 hours. - Upon completion of the reaction, the hot reaction mixture was filtered through diatomaceous earth. - The filtrate was evaporated to dryness to afford the target product 4-methoxypyridine-2-aldehyde (3.01 g, 21.93 mmol, 62.9% yield). 1H NMR (400.132 MHz, DMSO) δ 3.93 (3H, s), 7.27 (1H, m), 7.44 (1H, d), 8.63 (1H, d), 9.96 (1H, s).

16665-38-6
120 suppliers
$13.00/250mg

16744-81-3
114 suppliers
$45.00/50mg

Yield: 89%

Reaction Conditions:

with manganese(IV) oxide in chloroform at 80; for 24 h;

Steps:

3.3-2 (3-2) Synthesis of 2-formyl-4-methoxypyridine
A rotor and MnO2 (23.1 g, 70% assay, 184 mmol) were placed in a 100 mL two-mouth reaction vessel, a Dimroth condenser was attached, and the mixture was vacuum dried while heating with a heat gun. To this, 2-hydroxymethyl-4-methoxypyridine (2.14 g, 15.4 mmol) and dry CHCl3 (25 mL) were added, and the mixture was heated under reflux at 80 ° C. for 24 hours. After confirming that no raw material remained by 1H NMR, the reaction vessel was returned to room temperature. After removing MnO2 by Celite filtration, the mixture was thoroughly washed with CHCl3, the filtrate was collected, concentrated on a rotary evaporator, and vacuum dried to obtain a brown oily substance (1.87 g, Yield 89%).

References:

JP2021/42188, 2021, A Location in patent:Paragraph 0076; 0078-0079

29681-43-4 Synthesis