Thionyl Chloride → 2-Methylpyridine-3-carbonyl chloride

HRID 43387Notes

Reaction equation

HRID 43387 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-28888c9382e4446bb381c41c5071db41
Source dataset
uspto-grants-2013_09
Patent number
US08536183B2

Reaction notes

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