Methyl acetoacetate → HCID 178498883, compound

HRID 2090827Notes

Reaction equation

HRID 2090827 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=O.COC(OC)[N:12]([CH3:14])C.O.[NH2:18]N>C(O)C>[CH3:5][C:3]1[C:2]([C:1]([O:7][CH3:8])=[O:6])=[CH:14][NH:12][N:18]=1

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 178498883HCID 178498883, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl acetoacetate (30.0 g) and dimethylformamide dimethylacetal (34.7 mL) was stirred at 100° C. for 12 hr, and the mixture was allowed to cool. Ethanol (500 mL) and hydrazine monohydrate (12.6 mL) were added to the reaction mixture at room temperature, and the mixture was heated under reflux for 12 hr. The mixture was allowed to cool, and concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure to give the title object compound (22.3 g, 61%) as a pale-yellow solid.

Workup

  1. temperatureto cool
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 12 hr
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2931f78376b1455c9aaf1fcfba25d64f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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