Sodium Methoxide → 6-Chloro-2-methoxypyridine-3-carbaldehyde

HRID 1626512Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O-:12].[Na+]>>[Cl:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([O:12][CH3:11])[N:9]=1

Participants

Reactant 2

HCID 10942334Sodium Methoxide

HCID 122593832,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 108559456-Chloro-2-methoxypyridine-3-carbaldehydeYield 71.3%

Conditions

Temperature: 55 °C

Procedure

2,6-Dichloronicotinaldehyde (1 g, 5.68 mmol) was diluted with sodium methoxide (11.4 mL, 5.68 mmol) (solution in methanol) and heated to 55° C. After stirring for 3 hours, the reaction was loaded directly onto a silica gel column and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 6-chloro-2-methoxynicotinaldehyde (0.695 g, 4.05 mmol, 71.3% yield).

Workup

washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-b31d62420af64f3f8455b2b395c74378
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

Loading…