Thionyl Chloride → 2-Methylpyridine-3-carbonyl chloride

HRID 2066115Notes

Reaction equation

HRID 2066115 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>>[CH3:1][C:2]1[C:7]([C:8]([Cl:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 6433732-Methylnicotinic acid

Product 1

HCID 129025982-Methylpyridine-3-carbonyl chlorideYield 100%

Procedure

2-methyl-3-pyridinecarboxylic acid (20 g, 146 mmol) was dissolved in thionyl chloride (60 ml, 822 mmol) and stirred at room temperature for 24 h. The reaction was concentrated under reduced pressure, to obtain the title compound as a white solid (28.1 g, 146 mmol). Acyl chloride was checked by quenching a sample in MeOH, LCMS showed methyl ester derivative. {[M+H]+=152}

Workup

  1. concentrationThe reaction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bb99735eee4d471ea604bb9e093f0119
Source dataset
uspto-grants-2012_10
Patent number
US08288388B2

Reaction notes

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