2-Hydroxy-4-oxo-4-phenylbutanoic acid → 4,5-dihydro-4-hydroxy-2-(2-hydroxybutyl)-6-phenylpyridazin-3(2H)-one
Reaction equation
[C:1]([CH2:9][CH:10]([OH:14])[C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:15]([CH2:17][CH:18]([OH:21])[CH2:19][CH3:20])[NH2:16]>C(O)CCC>[OH:14][CH:10]1[CH2:9][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:16][N:15]([CH2:17][CH:18]([OH:21])[CH2:19][CH3:20])[C:11]1=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 3.5 grams (18 mmol) of 3-benzoyl-2-hydroxy-propionic acid and 1.9 grams (18 mmol) of 1-hydrazino-2-butanol in 40 ml of n-butanol is refluxed under nitrogen at 120° C. for 18 hours. After evaporation of the solvent, the product is partitioned between ether and water. The ether layer is washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. The resulting residue is dissolved in 2% ethanol-chloroform and filtered through 200 grams of silica gel yielding after evaporation 4,5-dihydro-4-hydroxy-2-(2-hydroxybutyl)-6-phenylpyridazin-3(2H)-one, m.p. 92°-94° C.
Workup
- customAfter evaporation of the solvent
- customthe product is partitioned between ether and water
- washThe ether layer is washed with aqueous sodium bicarbonate and brine
- dry with materialdried over magnesium sulfate
- customevaporated
- dissolutionThe resulting residue is dissolved in 2% ethanol-chloroform
- filtrationfiltered through 200 grams of silica gel yielding
- customafter evaporation 4,5-dihydro-4-hydroxy-2-(2-hydroxybutyl)-6-phenylpyridazin-3(2H)-one, m.p. 92°-94° C.
Sources & evidence
- ORD record
- ord-795c59f2dd2e4ef897c40618018f9087
- Source dataset
- uspto-grants-1979_12
- Patent number
- US04177273
Reaction notes
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