ChemicalBook CAS DataBase List 6-Chloro-4-methoxypyridine-3-carbaldehyde

6-Chloro-4-methoxypyridine-3-carbaldehyde synthesis

8synthesis methods

Product Name:6-Chloro-4-methoxypyridine-3-carbaldehyde
CAS Number:1256823-05-8
Molecular formula:C7H6ClNO2
Molecular Weight:171.58

1060811-62-2

124-41-4

6-Chloro-4-methoxypyridine-3-carbaldehyde

1256823-05-8

Sodium methanolate (0.068 g, 1.25 mmol) was added batchwise to a stirred solution of 4,6-dichloropyridine-3-carbaldehyde (0.2 g, 1.14 mmol) in methanol (10 mL) at 0 °C. The reaction mixture was slowly warmed to room temperature (about 5 hours) and stirring was continued at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was dissolved in dichloromethane. Insoluble solids were removed by filtration and the filtrate was purified by fast silica gel column chromatography with an elution gradient of 0 to 50% ethyl acetate in heptane solution. The purified grades were collected and concentrated under reduced pressure to give 6-chloro-4-methoxynicotinaldehyde (0.111 g, 57% yield) as a white solid.1H NMR (500 MHz, CDCl3, 22 °C) δ 4.02 (3H, s), 6.97 (1H, s), 8.69 (1H, s), 10.37 (1H, d). Mass spectrum (ESI+): m/z 172 [M+H]+.

1060811-62-2
136 suppliers
$15.00/100mg

124-41-4 Synthesis

124-41-4
729 suppliers
$12.00/25g

1256823-05-8
51 suppliers
$95.00/250mg

Yield:1256823-05-8 57%

Reaction Conditions:

in methanol at 0 - 25; for 21 h;Inert atmosphere;

Steps:

7 Preparation of 6-chloro-4-methoxynicotinaldehyde

Sodium methoxide (0.068 g, 1.25 mmol) was added portionwise to a stirred solution of 4,6-dichloronicotinaldehyde (0.2 g, 1.14 mmol) in MeOH (10 mL) cooled to 0°C. The reaction was allowed to warm to room temperature (over 5 hours) and stirred at roomtemperature for 16 hours. The reaction was concentrated in vacuo and then dissolved in DCM. Solids were removed by filtration and the filtrate was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 6-chloro-4-methoxynicotinaldehyde (0.111 g, 57%) as a white solid. ‘H NMR (500 MHz, CDC13, 22 °C) 4.02 (3H, s), 6.97 (1H, s), 8.69 (1H, s),10.37 (1H, d). nz/z: ES+ [M+H]+ 172.

References:

WO2018/19793,2018,A1 Location in patent:Page/Page column 126; 127