Thionyl Chloride → 2-Chloronicotinic acid

HRID 259566Notes

Reaction equation

HRID 259566 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[NH2:15][C:16]1[C:17](=[O:22])[NH:18][CH:19]=[CH:20][CH:21]=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:15][C:16]1[C:17](=[O:22])[NH:18][CH:19]=[CH:20][CH:21]=1)=[O:6]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 762582-Chloronicotinic acidHCID 3223533-Amino-2-pyridinol

Product 2

HCID 762582-Chloronicotinic acidHCID 227547993-(2-Chloronicotinoylamino)-2-pyridone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The acid chloride of 2-chloronicotinic acid was prepared by refluxing 11 g. (0.07 mole) of 2-chloronicotinic acid in 80 ml. of thionyl chloride for 1.5 hours. After evaporating to dryness, the oily residue was dissolved in 50 ml. of ether. The ether solution was added to a stirred ice-cold solution of 7.7 g. (0.07 mole) of 3-amino-2-pyridone in 80 ml. of dry pyridine during 15 minutes. After 30 more minutes at ice temperature and 4 hours at room temperature, it was allowed to stand overnight in an open dish. The crystalline residue was extracted with water and the solid residue (12.9 g.) was collected and recrystallized from dimethyl formamide-ether to give gray crystals of 3-(2-chloronicotinoylamino)-2-pyridone, m.p. 295° C.

Workup

  1. temperatureby refluxing 11 g
  2. customAfter evaporating to dryness
  3. dissolutionthe oily residue was dissolved in 50 ml
  4. additionThe ether solution was added to a stirred ice-cold solution of 7.7 g
  5. customat ice temperature and 4 hours
  6. customat room temperature
  7. extractionThe crystalline residue was extracted with water
  8. customthe solid residue (12.9 g.) was collected
  9. customrecrystallized from dimethyl formamide-ether

Sources & evidence

ORD record
ord-252557763e2f41a999d2cc9410e695e1
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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