Phosphorus oxychloride → Butyl 6-chloropyridazine-3-carboxylate

HRID 1870766Notes

Reaction equation

HRID 1870766 reaction equation
P(Cl)(Cl)([Cl:3])=O.O=[C:7]1[NH:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[CH:9]=[CH:8]1>C(#N)C.O>[Cl:3][C:7]1[N:12]=[N:11][C:10]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12346430Butyl 1,6-dihydro-6-oxo-3-pyridazinecarboxylate

Product 1

HCID 22622489Butyl 6-chloropyridazine-3-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of phosphorus oxychloride (20 ml) and acetonitrile (40 ml) heated at reflux was added a solution of n-butyl 6-oxo-1,6-dihydropyridazine-3-carboxylate (20 g) in acetonitrile (80 ml). The reaction was heated at reflux for 30 minutes, cooled and added to an ice cooled solution of K2C03 (87.8 g) in water (600 ml) with vigorous stirring. The product was filtered off, washed with water and dried at 60° C. to give n-butyl 6-chloropyridazine-3-carboxylate (17.5 g, 80% yield), mpt 110-111° C.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureThe reaction was heated
  4. temperatureat reflux for 30 minutes
  5. temperaturecooled
  6. filtrationThe product was filtered off
  7. washwashed with water
  8. customdried at 60° C.

Sources & evidence

ORD record
ord-87eff584b3e146b9828cd7e6cb639779
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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