Thionyl Chloride → HCID 178521114, compound

HRID 377016Notes

Reaction equation

HRID 377016 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, compound2×

Product 1

HCID 178521114HCID 178521114, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

13.92 g (0.1 mol) of 6-hydroxynicotinic acid and 0.04 g (0.5 mmol) of pyridine were heated in 60 ml of acetonitrile to 80° C. 12.49 g (0.105 mol) of thionyl chloride was instilled and the reaction again stirred for 30 minutes at 80° C. After cooling, the precipitate was filtered off, washed twice each with 10 ml of cold acetonitrile and concentrated by evaporation in a vacuum. 13.38 g (0.085 mol) of 6-hydroxynicotinoyl chloride was obtained as a light yellowish powder, corresponding to a yield of 85 percent relative to the 6-hydroxynicotinic acid. Further data concerning the product was:

Workup

  1. customthe reaction
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washwashed twice each with 10 ml of cold acetonitrile
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-bd0575c858a14da3b40a5d7612868a1d
Source dataset
uspto-grants-2000_02
Patent number
US06022974

Reaction notes

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