3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 1-(Pyridin-3-yl)heptan-1-one

HRID 660140Notes

Reaction equation

HRID 660140 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.C[N-]OC.[CH2:15]([Li])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2](=[O:9])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:4]=1

Participants

4

Reactant 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 53630747Methoxy-methyl amideHCID 178506865HCID 178506865, compound

Product 1

HCID 2227091-(Pyridin-3-yl)heptan-1-one

Procedure

In an example of the general procedure (scheme 1), nicotinoyl chloride hydrochloride (1) is converted to the N-methyl-N-methoxyamide (2) in the presence of a base and reacted with hexyl-lithium (J. Med. Chem., 35, 1992, 2392-2406) to produce 1-pyridin-3-yl-heptan-1-one (3).

Sources & evidence

ORD record
ord-e539eadc30454b1f98a367b86cc3d6a6
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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