(3,4-Dichlorobenzyl)hydrazine → 3-Amino-1-(3,4-dichlorobenzyl)-pyrazol-5-one
Reaction equation
CO[C:3](=[O:9])[CH:4]=[C:5]([NH2:8])OC.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:14][NH:15][NH2:16]>O1CCOCC1>[NH2:8][C:5]1[NH:16][N:15]([CH2:14][C:13]2[CH:17]=[CH:18][C:19]([Cl:20])=[C:11]([Cl:10])[CH:12]=2)[C:3](=[O:9])[CH:4]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
144 g (10% excess) of β-amino-β-methoxyacrylic acid methyl ester are introduced into 500 ml of dioxane. 191 g of 3,4-dichlorobenzylhydrazine are introduced into the reaction mixture while flushing with nitrogen. The mixture is stirred for 2 hours at 60°, the solvent is driven off on a rotary evaporator, the residue is worked with 600 ml of 2 N NaOH and extracted with ether, and the aqueous phase is stirred with animal charcoal of one-half hour. After filtration, the mixture is adjusted to pH 5 with dilute acetic acid. The product which initially is obtained as an oil becomes crystalline on rubbing and is finally purified by recrystallising it again from alcohol. 139 g, corresponding to about 54% of theory, of the compound identified above, as felted colorless needles of melting point 159° are obtained.
Workup
- customwhile flushing with nitrogen
- customthe solvent is driven off on a rotary evaporator
- extractionextracted with ether
- stirringthe aqueous phase is stirred with animal charcoal of one-half hour
- filtrationAfter filtration
- customThe product which initially is obtained as an oil
- customis finally purified
- customby recrystallising it again from alcohol
- customare obtained
Sources & evidence
- ORD record
- ord-4df03be351ee463d846369f5d6c79822
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03950528
Reaction notes
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