Methanol → HCID 178498433, compound

HRID 1479754Notes

Reaction equation

HRID 1479754 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:15]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([O:7][CH3:15])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178524562HCID 178524562, compound

Product 1

HCID 178498433HCID 178498433, compoundYield 78%

Procedure

To a solution of 2-hydroxyisonicotinic acid (1.4 g, 10 mmol) in methanol (100 mL) was added thionyl chloride (5.73 g, 40 mmol) at 0° C., the mixture was stirred overnight. The solvent was evaporated in vacuo and water was added. The mixture was extracted with ethyl acetate (100 mL×3), the organic phase was dried sodium sulfate and evaporated in vacuo to give methyl 2-hydroxyisonicotinate (1.2 g, 78%). LRMS (M+H+) m/z: calcd 153.04. found 153.

Workup

  1. customThe solvent was evaporated in vacuo and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (100 mL×3)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0bec6adcf8a6425a89363f65036a408a
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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