Ethyl Acetoacetate → HCID 20361945, compound

HRID 1679754Notes

Reaction equation

HRID 1679754 reaction equation
C(O[C:4](=[O:9])[CH2:5][C:6]([CH3:8])=O)C.[CH3:10][CH:11]([NH:19][NH2:20])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1>C(O)C>[CH3:8][C:6]1[NH:20][N:19]([CH:11]([CH3:10])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[C:4](=[O:9])[CH:5]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 12489385HCID 12489385, compound

Product 1

HCID 20361945HCID 20361945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

26 g of acetoacetic acid ethyl ester were dissolved in 20 ml of absolute ethanol. 30.0 g of α-methyl-4-methylbenzylhydrazine in a little absolute ethanol were slowly added to this solution under nitrogen. After the exothermic reaction had subsided, the mixture was heated for 2 hours under reflux. On cooling, the crude product crystallized out and was purified by recrystallization from methanol. Melting point 144°-146° C; yield 28 g (65% of theory).

Workup

  1. customAfter the exothermic reaction
  2. temperaturethe mixture was heated for 2 hours
  3. temperatureunder reflux
  4. temperatureOn cooling
  5. customthe crude product crystallized out
  6. customwas purified by recrystallization from methanol

Sources & evidence

ORD record
ord-e25f2ff490944f07953391359dbcbda2
Source dataset
uspto-grants-1978_03
Patent number
US04081596

Reaction notes

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