Oxalyl chloride → 2-Methylpyridine-3-carbonyl chloride

HRID 912355Notes

Reaction equation

HRID 912355 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:14])=O>CN(C=O)C.C(#N)C>[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:14])=[O:5]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 6433732-Methylnicotinic acid

Product 1

HCID 129025982-Methylpyridine-3-carbonyl chlorideYield 103.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile solution (5 ml) of 2-methylnicotinic acid (400 mg, 2.92 mmol) and DMF (11.2 μl, 0.156 mmol), oxalyl dichloride (501 μl, 5.83 mmol) was added dropwise, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, to obtain a crude product of 2-methylnicotinic acid chloride as a yellow liquid (470 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7fd086e5e11647fdba23723586a53760
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

Loading…