Dimethylamine → 6-Chloro-2-(dimethylamino)pyridine-3-carbaldehyde

HRID 1626529Notes

Reaction equation

HRID 1626529 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][NH:12][CH3:13]>>[Cl:10][C:8]1[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([N:12]([CH3:13])[CH3:11])[N:9]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 122593832,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 706995566-Chloro-2-(dimethylamino)pyridine-3-carbaldehydeYield 29.6%

Conditions

Temperature
50 °C

Procedure

2,6-Dichloronicotinaldehyde (500 mg, 2.84 mmol) was diluted with dimethylamine (3125 μL, 6.25 mmol) and heated to 50° C. After stirring for 3 hours, the reaction was loaded onto a silica gel column and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 6-chloro-2-(dimethylamino)nicotinaldehyde (155 mg, 0.840 mmol, 29.6% yield).

Workup

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

Sources & evidence

ORD record
ord-8b49c0e35fcb498091f6a9751b06931b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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