Water → Butyl 1,6-dihydro-6-oxo-3-pyridazinecarboxylate

HRID 1604372Notes

Reaction equation

HRID 1604372 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]([OH:10])=[O:9])[CH:4]=[CH:3]1.S(=O)(=O)(O)O.O>C(OC(C)=O)CCC.C(O)CCC>[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]([O:10][CH2:2][CH2:3][CH2:4][CH3:5])=[O:9])[CH:4]=[CH:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 3059706-Hydroxypyridazine-3-carboxylic Acid

Product 1

HCID 12346430Butyl 1,6-dihydro-6-oxo-3-pyridazinecarboxylateYield 170.5%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 31272Butyl AcetateSolvent

Procedure

A solution of 6-oxo-1,6-dihydropyridazine-3-carboxylic acid (British patent no. 856409) (52 g, 0.33 mol) in nBuOAc (80 ml) and butanol (80 ml) was treated with concentrated sulphuric acid (5 ml). The mixture was heated at reflux under a Dean-Stark trap. After 5 hours water production had ceased. The reaction was allowed to cool to ambient temperature and after standing overnight, the precipitate was filtered, washed with diethyl ether and dried to give butyl 6-oxo-1,6-dihydropyridazine-3-carboxylate as a white solid (55.2 g, 85%) m.p. 81-83° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under a Dean-Stark trap
  3. filtrationthe precipitate was filtered
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-f5787f32d5224c258f10db99ed4a4fee
Source dataset
uspto-grants-1999_11
Patent number
US05994353

Reaction notes

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