Thionyl Chloride → HCID 178521114, compound

HRID 1670522Notes

Reaction equation

HRID 1670522 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>C(#N)C.N1C=CC=CC=1>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 178418479HCID 178418479, compound

Product 1

HCID 178521114HCID 178521114, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Mix 6-hydroxy-nicotinic acid (14 g, 101 mmol) and pyridine (0.41 mL, 0.49 mmol) in acetonitrile (60 mL). Heat the mixture at 80° C. for 30 min. Add thionyl chloride (7.6 mL, 104 mmol) and continue heating at 80° C. for an additional 1.5 h. Cool to room temperature (reaction solidifies). Filter off the solid using a minimal amount of cold acetonitrile. Dry the solid in vacuo to obtain the desired intermediate as a tan solid (11.2 g, 70%).

Workup

  1. temperatureCool to room temperature
  2. custom(reaction solidifies)
  3. filtrationFilter off the solid
  4. customDry the solid in vacuo

Sources & evidence

ORD record
ord-2aec699cdabb44509e92e7e33b7c5c22
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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