Methanol → HCID 87427012, compound

HRID 715363Notes

Reaction equation

HRID 715363 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([O:15][CH2:16][CH:17]([F:19])[F:18])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12].[CH3:20]O>>[Cl:5][C:6]1[C:7]([O:15][CH2:16][CH:17]([F:19])[F:18])=[N:8][CH:9]=[C:10]([CH:14]=1)[C:11]([O:13][CH3:20])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 75480831HCID 75480831, compound

Product 1

HCID 87427012HCID 87427012, compoundYield 99%

Procedure

Thionyl chloride (1.38 ml, 18.9 mmol) is added to a solution of 5-chloro-6-(2,2-difluoroethoxy)nicotinic acid (1.5 g, 6.31 mmol, Step-1) in methanol (100 ml) at 0° C. Then the reaction mixture is refluxed with stirring for 2 hours. After removing solvent to give 1.57 g (>99% yield) of the title compound as white solid.

Workup

  1. temperatureThen the reaction mixture is refluxed
  2. customAfter removing solvent

Sources & evidence

ORD record
ord-9f0e23d0b378463d97514e3f2079a41a
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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