Sulfuric Acid → Butyl 1,6-dihydro-6-oxo-3-pyridazinecarboxylate

HRID 1870765Notes

Reaction equation

HRID 1870765 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[CH:4]=[CH:3]1.C(O[CH2:15][CH2:16][CH2:17][CH3:18])(=O)C.OS(O)(=O)=O>C(O)CCC>[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]([O:10][CH2:15][CH2:16][CH2:17][CH3:18])=[O:9])[CH:4]=[CH:3]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 31272Butyl AcetateHCID 3059706-Hydroxypyridazine-3-carboxylic Acid

Product 1

HCID 12346430Butyl 1,6-dihydro-6-oxo-3-pyridazinecarboxylateYield 79.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6-oxo-1,6-dihydropyridazine-3-carboxylic acid (117.24 g) [Ref: British Patent 856, 409], n-butyl acetate (293 ml), n-butanol (410 ml) and conc. H2SO4 (5.9 ml) was heated at reflux for 1 hour. The solvent was evaporated and the residue washed with n-butyl acetate to give n-butyl 6-oxo-1,6-dihydropyridazine-3-carboxylate (130.6 g, 79.6% yield), mpt 79-80° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was evaporated
  4. washthe residue washed with n-butyl acetate

Sources & evidence

ORD record
ord-ea87e22d7904471982cde7e1b178a1f1
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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