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ChemicalBook CAS DataBase List METHYL 6-FORMYLNICOTINATE
10165-86-3

METHYL 6-FORMYLNICOTINATE synthesis

8synthesis methods
Methyl 6-(hydroxymethyl)nicotinate

56026-36-9

METHYL 6-FORMYLNICOTINATE

10165-86-3

General procedure for the synthesis of methyl 6-formylnicotinate from methyl 6-hydroxymethylnicotinate: a mixture of methyl 6-hydroxymethylnicotinate (7 g, 37 mmol) and manganese dioxide (32.3 g, 372 mmol) in dichloromethane (200 mL) was stirred and reacted for 4 hours at 20°C. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to afford methyl 6-formylnicotinate (6 g, 97% yield). Mass spectral data: MS-ESI (m/z): 166.2 ([M + H]+) (LC-MS method C; retention time: 0.36 min).

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Yield:10165-86-3 97%

Reaction Conditions:

with manganese(IV) oxide in dichloromethane at 20; for 4 h;

Steps:

c (c) methyl 6-formylnicotinate

A mixture of methyl 6-(hydroxymethyl)nicotinate (7 g , 37 mmol) and Mn02 (32,3 g , 372 mmol) in DCM ( 200 mL ) was stirred at 20 °C for 4 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE/EtOAc = 5/1) to afford methyl 6-formylnicotinate (6 g , 97%).MS-ESI (m/z): 166.2 (M+l) + (LC-MS method C; Ret. time: 0.36 min).

References:

WO2014/114185,2014,A1 Location in patent:Page/Page column 126

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