Thionyl Chloride → 2-Methoxypyridine-4-carbonyl chloride

HRID 1662173Notes

Reaction equation

HRID 1662173 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=1)[C:10](O)=[O:11]>C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=1)[C:10]([Cl:3])=[O:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 8199422-Methoxyisonicotinic Acid

Product 1

HCID 193619212-Methoxypyridine-4-carbonyl chlorideYield 46%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Thionyl chloride (30.0 mL, 0.39 mol) was added to a suspension of 2-methoxy-isonicotinic acid (15.0 g, 97.9 mmol) in anhydrous toluene (150 mL). The mixture was heated at 80° C. under nitrogen for 3 hours, cooled to room temperature and filtered. The filtrate was concentrated in vacuo to afford the title compound 7.7 g (46% yield).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fa87cee453c74028962bd64ba9e7a046
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

Loading…